1-(2-Hydroxyethyl)piperazine → HCID 59792813, compound

HRID 31525Notes

Reaction equation

HRID 31525 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[N:20]([C:29]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37]Cl)=[CH:33][CH:32]=3)=[O:30])[C:19]([C:39]3[CH:44]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:42]=[CH:41][C:40]=3[O:49][CH2:50][CH3:51])=[N:18]2)=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH:21]([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[N:20]([C:29]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37][N:7]4[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]4)=[CH:33][CH:32]=3)=[O:30])[C:19]([C:39]3[CH:44]=[C:43]([C:45]([F:46])([F:47])[F:48])[CH:42]=[CH:41][C:40]=3[O:49][CH2:50][CH3:51])=[N:18]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 81531DiisopropylethylamineHCID 86595531[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-5-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-(4-chloromethyl-phenyl)-methanone

Product 1

HCID 59792813HCID 59792813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(2-Hydroxyethyl)-piperazine (10 uL, 0.08 mmol) was added to a solution of [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-5-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-(4-chloromethyl-phenyl)-methanone (20 mg, 0.03 mmol) and diisopropylethylamine (7 uL, 0.04 mmol) in anhydrous dimethylformamide (1.0 mL). The mixture was stirred overnight at 80° C. Evaporation of the solvent and chromatography of the residue over silica gel using 1-5% methanol in methylene chloride gave [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-5-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-{(4-(2-hydroxyethyl)piperazine-1-yl)methyl}phenyl]methanone, which was dissolved in dilute hydrochloric acid (0.5 N, 1 mL) and lyophilized to give [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-5-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-{(4-(2-hydroxyethyl)piperazine-1-yl)methyl}phenyl]methanone hydrochloride as a off-white powder (21 mg, 98%). LR-MS (APCI): 726.1 [(M+H)+].

Workup

  1. customEvaporation of the solvent and chromatography of the residue over silica gel using 1-5% methanol in methylene chloride

Sources & evidence

ORD record
ord-3de73b9203204d98bfa9f892df806a20
Source dataset
uspto-grants-2008_09
Patent number
US07425638B2

Reaction notes

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