Acetyl chloride → HCID 54322952, compound

HRID 2288191Notes

Reaction equation

HRID 2288191 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:43]=[CH:42][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:32])[C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=3)[C@H:13]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=3)[CH2:12]2)=[CH:8][CH:7]=1>O>[C:1]([NH:5][C:6]1[CH:43]=[CH:42][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:32])[C:18]3[CH:19]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=3)[C@H:13]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=3)[CH2:12]2)=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 54473583HCID 54473583, compound

Product 1

HCID 54322952HCID 54322952, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. extractionthe separated oil was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporate in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a mixture of toluene and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-3b21ac83d9434dc1841a67cda0ccc90c
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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