CA1041120A - Process for the preparation of 2-amino-n-cyclohexyl-3,5-dibromo-n-methyl-benzylamine - Google Patents

Process for the preparation of 2-amino-n-cyclohexyl-3,5-dibromo-n-methyl-benzylamine

Info

Publication number: CA1041120A
Authority: CA; Canada
Prior art keywords: dibromo; amino; methyl; preparation; trimethyl
Prior art date: 1973-07-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA205,645A

Other languages

English (en)

French (fr)

Other versions

CA205645S (en

Inventor

Johannes Keck

Gerd Kruger

Helmut Pieper

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Dr Karl Thomae GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-07-26

Filing date

1974-07-25

Publication date

1978-10-24

1974-07-25 Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH

1978-10-24 Application granted granted Critical

1978-10-24 Publication of CA1041120A publication Critical patent/CA1041120A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 11
238000006243 chemical reaction Methods 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 9
239000002904 solvent Substances 0.000 claims description 3
OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 abstract description 5
GHUMSGGCKVMYGH-UHFFFAOYSA-N (2-amino-3,5-dibromophenyl)methanol Chemical compound NC1=C(Br)C=C(Br)C=C1CO GHUMSGGCKVMYGH-UHFFFAOYSA-N 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
-1 phosphoryl halide Chemical class 0.000 abstract description 2
PAYDUUFACYKFRI-UHFFFAOYSA-N n-bis[cyclohexyl(methyl)amino]phosphoryl-n-methylcyclohexanamine Chemical compound C1CCCCC1N(C)P(=O)(N(C)C1CCCCC1)N(C)C1CCCCC1 PAYDUUFACYKFRI-UHFFFAOYSA-N 0.000 abstract 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
ZLDMZIXUGCGKMB-UHFFFAOYSA-N 3,5-dibromobenzaldehyde Chemical compound BrC1=CC(Br)=CC(C=O)=C1 ZLDMZIXUGCGKMB-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA205,645A 1973-07-26 1974-07-25 Process for the preparation of 2-amino-n-cyclohexyl-3,5-dibromo-n-methyl-benzylamine Expired CA1041120A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732337931 DE2337931A1 (de)	1973-07-26	1973-07-26	Neues verfahren zur herstellung von 2-amino-n-cyclohexyl-3,5-dibrom-n-methylbenzylamin

Publications (1)

Publication Number	Publication Date
CA1041120A true CA1041120A (en)	1978-10-24

Family

ID=5888014

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA205,645A Expired CA1041120A (en)	1973-07-26	1974-07-25	Process for the preparation of 2-amino-n-cyclohexyl-3,5-dibromo-n-methyl-benzylamine

Country Status (14)

Country	Link
JP (2)	JPS5515465B2 (cs)
AT (1)	AT330739B (cs)
BG (1)	BG24231A3 (cs)
CA (1)	CA1041120A (cs)
CH (1)	CH597147A5 (cs)
CS (2)	CS184839B2 (cs)
DE (1)	DE2337931A1 (cs)
DK (1)	DK135837C (cs)
ES (1)	ES427954A1 (cs)
FI (1)	FI177674A7 (cs)
HU (2)	HU167868B (cs)
NL (1)	NL7409046A (cs)
PL (1)	PL94273B1 (cs)
SE (2)	SE7409685L (cs)

1973
- 1973-07-26 DE DE19732337931 patent/DE2337931A1/de active Pending
1974
- 1974-06-11 FI FI1776/74A patent/FI177674A7/fi unknown
- 1974-06-20 AT AT510674A patent/AT330739B/de not_active IP Right Cessation
- 1974-06-25 CS CS7500001285A patent/CS184839B2/cs unknown
- 1974-06-25 CS CS4467A patent/CS170115B2/cs unknown
- 1974-06-28 BG BG031992A patent/BG24231A3/xx unknown
- 1974-07-04 NL NL7409046A patent/NL7409046A/xx not_active Application Discontinuation
- 1974-07-04 ES ES427954A patent/ES427954A1/es not_active Expired
- 1974-07-23 DK DK397274A patent/DK135837C/da active
- 1974-07-24 HU HUTO972A patent/HU167868B/hu unknown
- 1974-07-24 CH CH1023574A patent/CH597147A5/xx not_active IP Right Cessation
- 1974-07-24 HU HUTO1000A patent/HU168460B/hu unknown
- 1974-07-25 JP JP8559074A patent/JPS5515465B2/ja not_active Expired
- 1974-07-25 SE SE7409685A patent/SE7409685L/xx unknown
- 1974-07-25 PL PL1974173005A patent/PL94273B1/pl unknown
- 1974-07-25 CA CA205,645A patent/CA1041120A/en not_active Expired
1977
- 1977-09-01 SE SE7709869A patent/SE7709869L/xx unknown
1978
- 1978-01-24 JP JP664878A patent/JPS53101344A/ja active Pending

Also Published As

Publication number	Publication date
ATA510674A (de)	1975-10-15
SE7709869L (sv)	1977-09-01
DE2337931A1 (de)	1975-02-13
JPS5047945A (cs)	1975-04-28
HU168460B (cs)	1976-04-28
JPS5515465B2 (cs)	1980-04-23
CS170115B2 (cs)	1976-08-27
NL7409046A (nl)	1975-01-28
DK135837C (da)	1977-12-05
DK135837B (da)	1977-07-04
PL94273B1 (cs)	1977-07-30
FI177674A7 (cs)	1975-01-27
HU167868B (cs)	1975-12-25
DK397274A (cs)	1975-04-01
AT330739B (de)	1976-07-12
CH597147A5 (cs)	1978-03-31
CS184839B2 (en)	1978-09-15
BG24231A3 (bg)	1978-01-10
JPS53101344A (en)	1978-09-04
SE7409685L (cs)	1975-01-27
ES427954A1 (es)	1976-09-01

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DE2802387C2 (de)	1980-04-03	Verfahren zur Herstellung von Thiazo-üdin-4-on-essigsäure-Derivaten
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AT228216B (de)	1963-07-10	Verfahren zur Herstellung von neuen, carboxylhaltigen Amidinen
SU417939A3 (cs)	1974-02-28
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