2-Acetylbenzoic acid → HCID 54325049, compound

HRID 2288182Notes

Reaction equation

HRID 2288182 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][CH:41]=[CH:40][C:36]=1[C:37](O)=[O:38])(=[O:34])[CH3:33].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:32]([C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[C:37]([N:11]1[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]2[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]=2)[C@H:9]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=2)[CH2:10]1)=[O:38])(=[O:34])[CH3:33]

Participants

7

Reactant 5

HCID 684742-Acetylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54478438(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine

Product 1

HCID 54325049HCID 54325049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(2R-1-[3,5-Bis(trifluoromethyl)benzoyl)-2-(3,4-dimethylbenzyl)piperazine fumarate (785 mg) was added to a mixture of 2N sodium hydroxide solution (5 ml) and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine. A solution of this piperazine in N,N-dimethylformamide (7 ml) was added to a mixture of 2-acetylbenzoic acid (230 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (295 mg) and 1-hydroxybenzotriazole (208 mg) in N,N-dimethylformamide (3 ml) and the whole was stirred at room temperature overnight. The mixture was poured into a saturated sodium hydrogen carbonate solution (78 ml) and the resulting precipitates were filtered off. The filtrate was evaporate din vacuo to give (2R)-4-(2-acetylbenzoyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (0.45 g) as a powder.

Workup

  1. customthe resulting precipitates
  2. filtrationwere filtered off
  3. customThe filtrate was evaporate din vacuo

Sources & evidence

ORD record
ord-35fcde77ee994ad994fa371959a1a314
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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