Potassium Carbonate → HCID 53751959, compound

HRID 2288195Notes

Reaction equation

HRID 2288195 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)=[O:7].Br[CH2:35][CH2:36][CH2:37][OH:38].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:31][C:28]([F:29])([F:30])[C:26]1[CH:25]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:27]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:35][CH2:36][CH2:37][OH:38])[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)=[O:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 54095749HCID 54095749, compound

Product 1

HCID 53751959HCID 53751959, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(2-naphthylmethyl)piperazine (1.0 g) and 3-bromopropanol (330 mg) in N,N-dimethylformamide (2.5 ml) was stirred at room temperature in the presence of powdered potassium carbonate (444 mg). After 17 hours, the reaction mixture was diluted with ethyl acetate (30 ml) and then washed successively with water and brine, and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(3-hydroxypropyl)-2-(2-naphthylmethyl)piperazine (1.19 g).

Workup

  1. washwashed successively with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-f30392ddaafb4e6cafc803adfdd9e772
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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