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

HRID 2371157Notes

Reaction equation

HRID 2371157 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-88f471986ee64953a4617ad2afd87436
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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