Trifluoroacetic acid → N-Phenyl-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide
Reaction equation
[NH:1]([C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]2)[CH2:12][CH2:11]1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[C:2]1([NH:1][C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]3)[CH2:14][CH2:15]2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
tert-Butyl (3S)-3-{[4-(anilinocarbonyl)piperazin-1-yl]methyl}piperidine-1-carboxylate (4.0 g) was added to a mixture of dichloromethane (20 ml) and TFA (20 ml) and the reaction mixture stirred for 2 h. The solvent was removed in-vacuo and the residue dissolved in dichloromethane (20 ml) and subsequently poured into hydrochloric acid solution (1N, 20 ml). The aqueous layer was basified using potassium carbonate and extracted with dichloromethane (3×15 ml). The organic layer was dried using a phase separation cartridge and the solvent removed under reduced pressure to afford the desired compound as a white foam white (2.0 g), which was used without further purification.
Workup
- customThe solvent was removed in-vacuo
- dissolutionthe residue dissolved in dichloromethane (20 ml)
- additionsubsequently poured into hydrochloric acid solution (1N, 20 ml)
- extractionextracted with dichloromethane (3×15 ml)
- customThe organic layer was dried
- customa phase separation cartridge
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-fed8536070314919bf2a48f7a7558081
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710224B2
Reaction notes
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