Tetrahydrofuran → 1-(2-Chloroethyl)-4-(methylsulfonyl)piperidine
Reaction equation
[CH3:1][S:2]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12]O)[CH2:7][CH2:6]1)(=[O:4])=[O:3].S(Cl)([Cl:16])=O.C1COCC1>ClC(Cl)C>[Cl:16][CH2:12][CH2:11][N:8]1[CH2:9][CH2:10][CH:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]1Participants
5
Conditions
- Temperature
- 74 °C
Procedure
A mixture of 2-(4-(methylsulfonyl)piperidin-1-yl)ethanol (620 mg, 2.99 mmol) and thionyl chloride (1.092 mL, 14.95 mmol) in dichloroethane (5 mL) was heated up at 74° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to provide the crude, to the crude was added THF (10 mL), the grey precipitate was observed and collected. The solid was dried under vacuum for 20 hour to provide the desired product as grey solid (400 mg, 59%). LCMS: m/e 226.1 (M+H)+, 1.00 min (method 6).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customto provide the crude
- customcollected
- customThe solid was dried under vacuum for 20 hour
Sources & evidence
- ORD record
- ord-e6d61111c8c8461bbff38de8667ff559
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846647B2
Reaction notes
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