Hydrochloric Acid → 2-(4-(4-Fluoro-3-(trifluoromethyl)phenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)-N,N-dimethylethanamine dihydrochloride

HRID 1685195Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)[Cl:36].[ClH:38].CO>>[ClH:36].[ClH:38].[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:18]=[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]([CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH:16]=2)=[CH:20][C:21]=1[C:26]([F:27])([F:28])[F:29]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 6344Dichloromethane

HCID 672648444-(1-(2-(Dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866416122-(4-(4-Fluoro-3-(trifluoromethyl)phenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)-N,N-dimethylethanamine dihydrochlorideYield 98.38%

Procedure

Combine a solution of 4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester (28.00 g; 1.00 equiv; 57.79 mmol) in DCM (280.00 mL; 4.37 mol) with a 4 M solution of hydrogen chloride in methanol (50.56 mL; 3.50 equiv; 202.25 mmol). Stir the green suspension at RT for 3 h. Evaporate the solvent, and add EA (100 mL) and evaporate again. Add EA (200 mL) and stir the suspension for 30 m. Filter on a glass fritted funnel to obtain the title compound (26.00 g; 56.85 mmol; 98.38% yield) as a green solid. m/z (M+H): 385.2

Workup

customEvaporate the solvent
additionadd EA (100 mL)
customevaporate again
stirringAdd EA (200 mL) and stir the suspension for 30 m
filtrationFilter on a glass fritted funnel

Sources & evidence

ORD record: ord-58b3fad1f655451d87b32e58731bcb0b
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148387B2

Reaction notes

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