Hydrochloric Acid → HCID 19429505, compound

HRID 1078402Notes

Reaction equation

[C:1]([Cl:4])(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[C:23]([CH3:24])=[C:22]([CH2:25][OH:26])[N:21]=[CH:20]2)([CH3:14])[CH3:13])=[CH:8][CH:7]=1.C(N(CC)CC)C.Cl>ClCCl.CCOCC>[ClH:4].[ClH:5].[C:1]([O:26][CH2:25][C:22]1[N:21]=[CH:20][N:19]([CH2:18][CH2:17][CH2:16][NH:15][C:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)([CH3:14])[CH3:13])[C:23]=1[CH3:24])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of acetyl chloride (8.7 g) in dichloromethane (35.5 ml) was added dropwise with stirring to a solution of 1-{3-[1-(4-chlorophenyl)-1-methylethylamino]propyl}-5-methylimidazol-4-yl-methanol (3.55 g) in dichloromethane (88.8 ml) containing triethylamine (11.1 g) at 0° C. The mixture was stirred at 0° C. for 30 minutes and then at ambient temperature for 2 hours. The mixture was diluted with dichloromethane, washed with 5M sodium hydroxide solution, dried and evaporated. The residue obtained was dissolved in ether and acidified with ethereal hydrogen chloride. The solid was collected by filtration and recrystallised from aqueous propan-1-ol to give 1-{3-[1-(4-chlorophenyl)-1-methylethylamino]propyl}-5-methylimidazol-4-ylmethyl acetate dihydrochloride, m.p. 188°-189° C.

Workup

waitat ambient temperature for 2 hours
washwashed with 5M sodium hydroxide solution
customdried
customevaporated
customThe residue obtained
filtrationThe solid was collected by filtration
customrecrystallised from aqueous propan-1-ol

Sources & evidence

ORD record: ord-00075ecd259840aaa479be6e23c773df
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05547972

Reaction notes

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