Hydrochloric Acid → HCID 88148173, compound

HRID 2288178Notes

Reaction equation

HRID 2288178 reaction equation
[C:1]([C:4]1[CH:42]=[CH:41][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:30])[C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)[C@H:11]([CH2:31][C:32]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][CH:33]=3)[CH2:10]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[ClH:43]>C(OCC)(=O)C>[ClH:43].[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:30])[C:16]3[CH:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)[C@H:11]([CH2:31][C:32]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][CH:33]=3)[CH2:10]2)=[CH:41][CH:42]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54395822HCID 54395822, compound

Product 1

HCID 88148173HCID 88148173, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (228 mg), 1-[4-(bromomethyl)phenyl]ethanone (107 mg) and potassium carbonate (42 mg) in acetonitrile (2 ml) was refluxed for 4.5 hours. After cooling, the mixture was evaporated in vacuo. Ethyl acetate and water were added to the residue and the organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of dichloromethane and methanol as an eluent to give (2R)-4-(4-acetylbenzyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (0.30 g). To a solution of this piperazine (0.30 g) in ethyl acetate was added 4N hydrogen chloride in ethyl acetate solution (0.13 ml) and the whole was evaporated in vacuo. The residue was triturated with a mixture of ethyl acetate and ether to give (2R)-4-(4-acetylbenzyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine hydrochloride (283.5 mg) as a powder.

Workup

  1. customthe whole was evaporated in vacuo
  2. customThe residue was triturated with a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-710acf23924a4bb9bb61e4724d1040f0
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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