Triethylamine → [1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[CH2:16][CH2:17][OH:18].C(N(CC)CC)C.ClCCl.CO>C(#N)C>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:16][CH2:17][OH:18])[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
A mixture of tert-butyl piperidin-4-ylcarbamate (5 g, 25 mmol), 2-bromoethanol (1.77 mL, 25 mmol) and triethylamine (3.86 mL, 27.5 mmol) in acetonitrile (20 mL) was heated in a sealed tube at 50° C. for 16 hours. The solvent was removed under reduced pressure, and the residue was taken up in ethyl acetate (300 mL) and washed with saturated aqueous sodium hydrogen carbonate solution (100 mL). The aqueous phase was back-extracted once with ethyl acetate (100 mL) and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with dichloromethane/methanol (4:1) gave 4.04 g (66% yield) of product as a colorless solid, mp 66° C.
Workup
- customThe solvent was removed under reduced pressure
- washwashed with saturated aqueous sodium hydrogen carbonate solution (100 mL)
- extractionThe aqueous phase was back-extracted once with ethyl acetate (100 mL)
- dry with materialthe combined organic phases were dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-813b98a727f145e5b8110ec96fbc329e
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124602B2
Reaction notes
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