2-Methoxyethylamine → N-2-methoxyethyl-1-benzyloxycarbonylpiperidine-4-oxyacetamide
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([O:21]CC)=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][CH2:26][CH2:27][NH2:28]>>[CH3:24][O:25][CH2:26][CH2:27][NH:28][C:19](=[O:21])[CH2:18][O:17][CH:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][CH2:15]1Participants
Procedure
A mixture of ethyl 1-benzyloxycarbonylpiperidine-4-oxyacetate (2.4 g) and 2-methoxyethylamine (5 ml) was heated on a steam bath for 6 hours. The amine was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (10 ml), washed sequentially with dilute citric acid solution (5 ml), water (5 ml) and saturated aqueous sodium chloride (5 ml), dried (MgSO4) and concentrated. The residual oil was purified by flash column chromatography, eluting with hexane/ethyl acetate (1:3) to give N-2-methoxyethyl-1-benzyloxycarbonylpiperidine-4-oxyacetamide (500 mg) as a colourless oil. NMR: (d6DMSO): δ 1.4-1.5(2H,m); 1.75-1.9(2H,m); 3.0-3.4(9H,m); 3.55(1H,m); 3.65-3.8(2H,m); 3.9(2H,s); 5.1(2H,s); 7.3(5H,m); 7.6(1H, br. t); m/e 351(M+H)+, 373 (M+Na)+.
Workup
- temperaturewas heated on a steam bath for 6 hours
- customThe amine was evaporated under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate (10 ml)
- washwashed sequentially with dilute citric acid solution (5 ml), water (5 ml) and saturated aqueous sodium chloride (5 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residual oil was purified by flash column chromatography
- washeluting with hexane/ethyl acetate (1:3)
Sources & evidence
- ORD record
- ord-e3237f44a7c647e38fe82f96a1f57f8d
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753659
Reaction notes
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