Diethyl Ether → 4-Benzyl-1-(2-benzyloxycarbonylamino-ethyl)-piperidine-4-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:19]([O:26][C:27](=[O:32])[NH:28][CH2:29][CH2:30]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C.CCOCC>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH2:8][N:9]([CH2:30][CH2:29][NH:28][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:32])[CH2:10][CH2:11]1)=[O:5])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
4-Benzyl-piperidine-4-carboxylic acid ethyl ester (2.5 g, 10 mmol), (2-bromo-ethyl)-carbamic acid benzyl ester (2.58 g, 10 mmol) and DIPEA (1.7 mL, 10 mmol) are dissolved in THF (50 mL) and heated at 80° C. for 15 h. The mixture is poured into Et2O (200 mL) and washed with sat. Na2CO3 (50 mL). The ether phase is extracted with 1M aqueous HCl (3×50 mL), the aqueous extracts washed with ether (50 mL) and adjusted to pH 14 with cooled 33% aqueous NaOH. The aqueous phase is extracted with CH2Cl2 (4×50 mL). The organic extracts are dried (Na2SO4), filtered and evaporated to provide the title compound.
Workup
- washwashed with sat. Na2CO3 (50 mL)
- extractionThe ether phase is extracted with 1M aqueous HCl (3×50 mL)
- washthe aqueous extracts washed with ether (50 mL)
- temperaturewith cooled 33% aqueous NaOH
- extractionThe aqueous phase is extracted with CH2Cl2 (4×50 mL)
- dry with materialThe organic extracts are dried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-6321cd404e1d42c98e78b5a8598096aa
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375227B2
Reaction notes
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