Hydrochloric Acid → {2-[4-(3-Chloro-4-fluoro-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-ethyl}-dimethyl-amine di hydrochloride

HRID 1685171Notes

Reaction equation

HRID 1685171 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:32].O1CCOCC1>C(Cl)Cl.CO>[ClH:26].[ClH:32].[Cl:26][C:21]1[CH:20]=[C:19]([C:17]2[N:18]=[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[N:15]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH:16]=2)[CH:24]=[CH:23][C:22]=1[F:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 672647824-(4-(3-chloro-4-fluorophenyl)-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86641602{2-[4-(3-Chloro-4-fluoro-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-ethyl}-dimethyl-amine di hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-(4-(3-chloro-4-fluorophenyl)-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester (194 mg; 0.43 mmol) in DCM (5 mL) and methanol (3 mL) and add 4 M hydrogen chloride in dioxane (5 mL; 20 mmol). Stir 30 min and evaporate; add DCM/MeOH and evaporate under vacuum to provide the title compound (245 mg) as a white solid. MS (ES): m/z=351 (M+H).

Workup

  1. customevaporate
  2. customadd DCM/MeOH and evaporate under vacuum

Sources & evidence

ORD record
ord-4ebf1dd7bb674af08c5a88ec88501f02
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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