Triethylamine → (1-Methylpiperidin-2-yl)methyl methanesulfonate
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][OH:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>O1CCCC1>[CH3:17][S:18]([O:9][CH2:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][N:2]1[CH3:1])(=[O:20])=[O:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-methyl-2-piperidine-methanol (Aldrich, 0.27 mL, 2.1 mmol) in 10 mL tetrahydrofuran (THF) at 0° C. was added triethylamine (0.87 mL, 6.22 mmol) followed by methanesulfonyl chloride (0.24 mL, 3.1 mmol). The mixture was stirred at 0° C. for 10 min then the ice-bath was removed and the reaction mixture was stirred at 23° C. for an additional 1.5 h. The reaction mixture was filtered though Celite with THF and concentrated under reduced pressure. This crude material was used directly in the next reaction.
Workup
- customthe ice-bath was removed
- stirringthe reaction mixture was stirred at 23° C. for an additional 1.5 h
- filtrationThe reaction mixture was filtered though Celite with THF
- concentrationconcentrated under reduced pressure
- customThis crude material was used directly in the next reaction
Sources & evidence
- ORD record
- ord-ddf79270667a4f8eba4cd55886d599b6
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750039B2
Reaction notes
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