Ethyl Bromide → Benzyl 4-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperazine-1-carboxylate
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]2)[CH2:2]1.Br[CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:25]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:12][CH2:13]2)[CH2:2]1)[CH3:26]Participants
5
Procedure
Benzyl 4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxylate (1.8 g), bromoethane (1.3 ml) and potassium carbonate (3.9 g) was refluxed in acetone (50 ml) for seven 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 dichloromethane (100 ml) and water (100 ml). The dichloromethane 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 (352 mg).
Workup
- filtrationthen filtered
- concentrationThe filtrate was concentrated in vacuo
- customthe resulting oil separated between dichloromethane (100 ml) and water (100 ml)
- customThe dichloromethane layer was separated
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationthen concentrated in vacuo onto silica gel (5 g)
Sources & evidence
- ORD record
- ord-c5dca568ac774fdca179ffc5fe58212f
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710224B2
Reaction notes
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