Triethylamine → HCID 54056206, compound

HRID 2288181Notes

Reaction equation

HRID 2288181 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7].[C:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=1)(=[O:34])[CH3:33].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl>[C:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39]([N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:4]=3)[C@H:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=3)[CH2:10]2)=[O:40])=[CH:37][CH:36]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 114704-Acetylbenzoic AcidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 54478438(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine

Product 1

HCID 54056206HCID 54056206, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (0.25 g) and 4-acetylbenzoic acid (0.09 g) in dichloromethane (8 ml) was added triethylamine (0.2 ml) at room temperature. 2-Chloro-1-methylpyridinium iodide (0.17 g) was added, and the mixture was stirred at room temperature for 2.5 hours. The resulting mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium bicarbonate solution and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography using ethyl acetate--n-hexane (1:1) as an eluent to afford (2R)-4-(4-acetylbenzoyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (0.31 g).

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c8abae9e01a047e48a56993fdcfc0eb4
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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