Hydrochloric Acid → 2-(4-(4-Chlorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)-N,N-dimethylethanamine tris hydrochloride

HRID 1685170Notes

Reaction equation

HRID 1685170 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:16]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:19]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1.C(Cl)Cl>[ClH:26].[ClH:1].[ClH:26].[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]2[N:19]=[C:15]([CH:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)[N:16]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH:17]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 672647474-(4-(4-Chlorophenyl)-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 672647962-(4-(4-Chlorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)-N,N-dimethylethanamine tris hydrochlorideYield 74.07%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4M HCl in 1,4-dioxane (2 mL) to 4-[4-(4-chloro-phenyl)-1-(2-dimethylamino-ethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.8 g; 0.0018 mol; 1.0 equiv), in DCM and stir at RT for 6 h. Concentrate the reaction, crystallize from diethyl ether and filter to get the title compound (0.6 g; 74.07%). MS (ES+): m/z=333 (M+H)

Workup

  1. concentrationConcentrate
  2. customthe reaction
  3. customcrystallize from diethyl ether
  4. filtrationfilter

Sources & evidence

ORD record
ord-cdcfcc5a73394bbc87d789577a21d393
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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