Ethyl Bromide → HCID 59846088, compound

HRID 549930Notes

Reaction equation

HRID 549930 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](Br)[CH3:33]>CN(C)C=O>[CH2:32]([N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:3]1)[CH3:33]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 67158336HCID 67158336, compound

Product 1

HCID 59846088HCID 59846088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(piperidin-3-ylcarbonyl)-4-[3-(trifluoromethyl)phenyl]piperazine hydrochloride (600 mg) in N,N-dimethylformamide (10 ml) was stirred at room temperature. Potassium carbonate (800 mg) was added followed by ethyl bromide (158 mg) and the mixture was stirred overnight. The mixture was filtered through a sinter and then through a SCX-2 column eluting with methanol and then a 7M solution NH3 in methanol. The basic fraction was concentrated at reduced pressure. This gave 1-[(1-ethylpiperidin-3-yl)carbonyl]-4-[3-(trifluoromethyl)phenyl]piperazine as a colourless oil (420 mg)

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationThe mixture was filtered through a sinter
  3. washthrough a SCX-2 column eluting with methanol
  4. concentrationThe basic fraction was concentrated at reduced pressure

Sources & evidence

ORD record
ord-d68f48b892064baa9eae2ed82b0b9054
Source dataset
uspto-grants-2011_05
Patent number
US07943768B2

Reaction notes

Loading…