Ethyl Bromide → N-(3,4-Dichlorophenyl)-4-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperazine-1-carboxamide

HRID 603199Notes

Reaction equation

HRID 603199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:26][CH3:27])[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 57656731N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide

Product 1

HCID 11553070N-(3,4-Dichlorophenyl)-4-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide (0.30 g), bromoethane (0.12 ml) and potassium carbonate (0.56 g) was refluxed in acetone (70 ml) for 18 hours. The reaction mixture was allowed to cool to room temperature then filtered. The filtrate was concentrated in vacuo and the resulting oil separated between ethyl acetate (100 ml) and water (100 ml). The ethyl acetate layer was separated, dried over magnesium sulphate, filtered then concentrated in vacuo onto silica gel (5 g). The resulting powder was subjected to chromatography on silica gel (50 g) using a gradient of 100% dichloromethane through to 20% methanolic ammonia in dichloromethane to give the title compound (24.9 mg).

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting oil separated between ethyl acetate (100 ml) and water (100 ml)
  4. customThe ethyl acetate layer was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationthen concentrated in vacuo onto silica gel (5 g)

Sources & evidence

ORD record
ord-d12df8844e724305b36e4e6192eb5ea4
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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