N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine

Base Information

• Chemical Name: N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine
• CAS No.: 1194488-55-5
• Molecular Formula: C₁₅H₂₂BrNO
• Molecular Weight: 312.25
• Mol file: 1194488-55-5.mol

Synonyms:N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine

Chemical Property of N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine

There total 8 articles about N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine 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:

3-bromo-N-cyclopropyl-5-(3-methoxypropyl)-4-methylbenzamide (1229245-21-9) → N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine (1194488-55-5)

Guidance literature:

3-bromo-N-cyclopropyl-5-(3-methoxypropyl)-4-methylbenzamide; With sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 19.8 - 35 ℃; for 21.5h; Inert atmosphere; Large scale reaction;

With hydrogenchloride; water; In tetrahydrofuran; at 20 - 50 ℃; for 4h; Inert atmosphere; Large scale reaction;

With sodium hydroxide; In water; pH=14; Large scale reaction;

DOI:10.1021/op2001063

Reference yield:

3-bromo-N-cyclopropyl-5-(3-methoxyprop-1-yn-1-yl)-4-methylbenzamide (1229245-18-4) → N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine (1194488-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: platinum(IV) oxide; hydrogen; triethylamine / toluene / 4.5 h / 20 - 35 °C / 2052.96 Torr / Autoclave; Large scale reaction

2.1: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 21.5 h / 19.8 - 35 °C / Inert atmosphere; Large scale reaction

2.2: 4 h / 20 - 50 °C / Inert atmosphere; Large scale reaction

2.3: pH 14 / Large scale reaction

With platinum(IV) oxide; sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex; hydrogen; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/op2001063

Reference yield:

3-bromo-5-iodo-4-methylbenzoic acid (1229245-20-8) → N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]cyclopropanamine (1194488-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 7 h / 60 °C / Inert atmosphere; Large scale reaction

2.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; ethyl acetate / 1.75 h / 9 - 19 °C / Inert atmosphere; Large scale reaction

3.1: platinum(IV) oxide; hydrogen; triethylamine / toluene / 4.5 h / 20 - 35 °C / 2052.96 Torr / Autoclave; Large scale reaction

4.1: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 21.5 h / 19.8 - 35 °C / Inert atmosphere; Large scale reaction

4.2: 4 h / 20 - 50 °C / Inert atmosphere; Large scale reaction

4.3: pH 14 / Large scale reaction

With platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; copper(l) iodide; boron trifluoride-tetrahydrofuran complex; hydrogen; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethyl acetate; toluene; 1.1: Sonogashira coupling;

DOI:10.1021/op2001063

upstream raw materials:

3-bromo-N-cyclopropyl-5-(3-methoxypropyl)-4-methylbenzamide

3-bromo-N-cyclopropyl-5-(3-methoxyprop-1-yn-1-yl)-4-methylbenzamide

3-bromo-5-iodo-4-methylbenzoic acid

3-bromo-5-(3-methoxyprop-1-yn-1-yl)-4-methylbenzoic acid

Downstream raw materials:

(3R,4S)-N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]-N-cyclopropyl-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-piperidine-3-carboxamide

tert-butyl (3R,4S)-3-{[[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl](cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate

(3R,4S)-N-[3-bromo-5-(3-methoxypropyl)-4-methylbenzyl]-N-cyclopropyl-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-piperidine-3-carboxamide hydrochloride

3-{3-bromo-5-[(cyclopropylamino)methyl]-2-methylphenyl}-1-propanol

Refernces

• 1、 -. "3, 4 - SUBSTITUTED PIPERIDINE DERIVATIVES AS RENIN INHIBITORS". Page/Page column 68. . Retrieved 2009/12/27.