Benzylamine → tert-Butyl 4-(2-(benzylamino)ethyl)piperidine-1-carboxylate
Reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)(=O)=O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([NH:8][CH2:14][CH2:15][CH:16]1[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:20][CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Procedure
Benzylamine (345 μl, 3.22 mmol, 1.1 eq) was added to a solution of tert-butyl 4-(2-(methyl-sulfonyloxy)ethyl)piperidine-1-carboxylate (0.9 g, 2.93 mmol, 1 eq) and triethylamine (0.8 ml, 5.86 mmol, 2 eq) in toluene (50 ml), and refluxing was carried out for 48 h. After monitoring by thin-layer chromatography, the reaction solution was concentrated and the residue was taken up in ethyl acetate (100 ml), washed with water (30 ml) and sat. NaCl solution (40 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, ethyl acetate), a yellow solid was obtained. Yield: 43% (400 mg, 1.25 mmol).
Workup
- temperaturerefluxing
- concentrationthe reaction solution was concentrated
- washwashed with water (30 ml) and sat. NaCl solution (40 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customAfter purification by column chromatography (silica gel, ethyl acetate)
- customa yellow solid was obtained
Sources & evidence
- ORD record
- ord-7facf08e13494e999317230af450ba91
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
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