Triethylamine → (1-Methylpiperidin-2-yl)methyl methanesulfonate

HRID 227369

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

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-a17f828435f94eff96c61b543cf3d75e
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560481B2

Linked notes

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