N-Methyl-N-(3-chloropropyl)homoveratrylamine

Base Information

• Chemical Name: N-Methyl-N-(3-chloropropyl)homoveratrylamine
• CAS No.: 36770-74-8
• Molecular Formula: C14H22 Cl N O2
• Molecular Weight: 271.787
• Hs Code.: 2922299090
• European Community (EC) Number: 253-198-8
• UNII: 1RK3H74O3Y
• DSSTox Substance ID: DTXSID001192363
• Nikkaji Number: J331.065E
• Wikidata: Q27252795
• Mol file: 36770-74-8.mol

Synonyms:36770-74-8;3-chloro-n-(3,4-dimethoxyphenethyl)-n-methylpropan-1-amine;N-Methyl-N-(3-chloropropyl)homoveratrylamine;3-CHLOROPROPYL-[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINE;3-chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylpropan-1-amine;N-METHYL-N-(3-CHLOROPROPYL)-3,4-DIMETHOXYPHENETHYLAMINE;UNII-1RK3H74O3Y;1RK3H74O3Y;Benzeneethanamine, N-(3-chloropropyl)-3,4-dimethoxy-N-methyl-;EINECS 253-198-8;N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamine;SR-45813;3-CHLORO-N-(2-(3,4-DIMETHOXYPHENYL)ETHYL)-N-METHYLPROPAN-1-AMINE;SCHEMBL3656443;DTXSID001192363;N-3-Chloropropyl-N-methyl-2-(3,4-dimethoxyphenyl)ethylamine;4-Morpholineethanamine,b,b-dimethyl-;MFCD08063812;AKOS015924579;SB81752;I11711;Q27252795;VERAPAMIL HYDROCHLORIDE IMPURITY D [EP IMPURITY];3-chloropropyl-(2-(3,4-dimethoxyphenyl)-ethyl)-methylamine;N-(3-chloropropyl)-3,4-dimethoxy-N-methyl-phenethylamine;N-(3-Chloropropyl)-3,4-dimethoxy-N-methylbenzeneethanamine;N-Methyl N-(3-chloropropyl)-3,4-dimethoxybenzenthylamine;n-methyl-n-(3-chloropropyl)-3,4-dimethoxyphenethyl amine;(3-CHLOROPROPYL)[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINE;3-Chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-propan-1-amine;1-Chloro-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane;3-[N-(2-(3,4-di-methoxyphenyl)-ethyl)-N-methylamino]-propylchloride;3-[N-(2-(3,4-dimethoxyphenyl)-ethyl)-N-methylamino]-propyl chloride;3-Chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-1-propanamine #;429691-49-6

Chemical Property of N-Methyl-N-(3-chloropropyl)homoveratrylamine

Chemical Property:

• Vapor Pressure: 2.02E-05mmHg at 25°C
• Boiling Point: 361.8°Cat760mmHg
• PKA: 8.80±0.50(Predicted)
• Flash Point: 172.6°C
• PSA: 21.70000
• Density: 1.066g/cm³
• LogP: 2.80700
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 271.1339066
• Heavy Atom Count: 18
• Complexity: 216

Purity/Quality:

99%, ^*data from raw suppliers

N-(3-Chloropropyl)-3,4-dimethoxy-N-methylbenzeneethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CCCCl)CCC1=CC(=C(C=C1)OC)OC
• Uses: N-(3-Chloropropyl)-3,4-dimethoxy-N-methylbenzeneethanamine (Verapamil EP Impurity D) is a reagent in the synthesis of Zatebradine, an anti-anginal agent.

Technology Process of N-Methyl-N-(3-chloropropyl)homoveratrylamine

There total 5 articles about N-Methyl-N-(3-chloropropyl)homoveratrylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-methylhomoveratrylamine (3490-06-0) + 1.3-chlorobromopropane (109-70-6) → N-(3-chloropropyl)-3,4-dimethoxy-N-methylphenethylamine (36770-74-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1021/jm00013a017

Reference yield:

benzenesulfonyl chloride (98-09-9) + 3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)amino]-propanol (85175-54-8) → N-(3-chloropropyl)-3,4-dimethoxy-N-methylphenethylamine (36770-74-8)

Guidance literature:

In dichloromethane;

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-(3-chloropropyl)-3,4-dimethoxy-N-methylphenethylamine (36770-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) PhCHO, 3.) 2N aq. NaOH

2: K₂CO₃ / dimethylformamide / 16 h / Ambient temperature

With sodium hydroxide; potassium carbonate; benzaldehyde; In N,N-dimethyl-formamide;

DOI:10.1021/jm00013a017

upstream raw materials:

N-methylhomoveratrylamine

1.3-chlorobromopropane

2-(3,4-dimethoxyphenyl)-ethylamine

benzenesulfonyl chloride

Downstream raw materials:

zatebradine

1-Isobutyryl-1-[4-{3-[N methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy}-benzenesulphonyl]cyclopropane

4-{3-[N-methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy}benzenesulphonylbenzene hydrochloride

Verapamil

Refernces

• 1、 Pauvert, Micka?l,Collet, Sylvain,Guingant, André. "Silver nitrate-promoted ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives: Application to the synthesis of the anti-anginal zatebradine". . p. 4203 - 4206. Retrieved 2007/10/03.
• 2、 Dodic, Nerina,Dumaitre, Bernard,Daugan, Alain,Pianetti, Pascal. "Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides". . p. 2418 - 2426. Retrieved 2007/10/02.