Toluene → N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine

HRID 323965Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C1(C)C=CC=CC=1>CC(N(C)C)=O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:12][CH2:11][C:10]([NH:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)([CH3:14])[CH3:13])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of 2-[3-(imidazol-1-yl)propylamino]-2-methyl-1-propanol (1.5 g) in dimethyl acetamide (10 ml) was added dropwise to a stirred suspension of sodium hydride (0.32 g of a 60% dispersion in mineral oil) in dimethyl acetamide (15 ml) at 30° C. under nitrogen. The mixture was stirred for 45 minutes at 30° C. and then a solution of 4-chlorobenzyl chloride (1.63 g) in dimethyl acetamide (5 ml) was added. After the addition, the mixture was heated at 100-105° C. for 30 minutes and then cooled to 25° C. Toluene (50 ml) was added and the mixture was washed with water. The toluene layer was extracted with 5M hydrochloric acid. The combined acid extracts were basified with concentrated sodium hydroxide solution with cooling and extracted with dichloromethane to give an oil which was distilled under high vacuum to give N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine, b.p. 180-185° C. at 0.3 mbar.

Workup

additionAfter the addition
temperaturethe mixture was heated at 100-105° C. for 30 minutes
temperaturecooled to 25° C
washthe mixture was washed with water
extractionThe toluene layer was extracted with 5M hydrochloric acid
temperaturewith cooling
extractionextracted with dichloromethane
customto give an oil which
distillationwas distilled under high vacuum

Sources & evidence

ORD record: ord-f13bd58339324978a6c842ef6a00ce81
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06215001B1

Reaction notes

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