Hydrochloric Acid → HCID 88169224, compound

HRID 2288192Notes

Reaction equation

HRID 2288192 reaction equation
[C:1]([NH:4][C:5]1[CH:42]=[CH:41][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:31])[C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=3)[C@H:12]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:11]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl>C(OCC)(=O)C>[ClH:39].[C:1]([NH:4][C:5]1[CH:42]=[CH:41][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:31])[C:17]3[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[C:19]([C:27]([F:28])([F:29])[F:30])[CH:18]=3)[C@H:12]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:11]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54322952HCID 54322952, compound

Product 1

HCID 88169224HCID 88169224, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Piridine (23 μl) and acetyl chloride (16 μl) were successively added to a solution of (2R)-4-(4-aminobenzyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorobenzyl)-piperazine (113 mg) and the whole was stirred at room temperature for 1.5 hours. The mixture was poured into water and the separated oil was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporate in vacuo. The residue was purified by column chromatography on silica gel with a mixture of toluene and ethyl acetate as an eluent to give (2R)-4-(4-acetylaminobenzyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorobenzyl)piperazine (98.3 mg). The obtained piperazine was dissolved in ethyl acetate. 4N Hydrogen chloride in ethyl acetate solution (43 μl) was added to the solution and the mixture was evaporated in vacuo. The residue was triturated with n-hexane to give (2R)-4-(4-acetylaminobenzyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dichlorobenzyl)piperazine hydrochloride (92 mg).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-48ebc9745e9b496ab0e3d487cc1fc696
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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