Triethylamine → 1-Benzoylpiperidin-4-ylmethyl methanesulfonate

HRID 1291196Notes

Reaction equation

HRID 1291196 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:16][CH2:15][CH:12]1[CH2:13][CH2:14][N:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:10][CH2:11]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 102628704-Piperidinemethanol, 1-benzoyl-

Product 1

HCID 99947861-Benzoylpiperidin-4-ylmethyl methanesulfonateYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7.5 g (0.0342 mol) of 1-benzoyl-4-hydroxymethyl-piperidine were dissolved in 170 ml of dichlormethane and 17 ml (0.122 mol) of triethylamine, cooled to 0° and treated with a solution of 3.14 ml (0.0404 mol) of methanesulfonyl chloride in 20 ml of dichloromethane. The mixture was stirred at 0° for 1/2 hr. Then, 100 ml of 1N aqueous HCI were added, the mixture was stirred for 5 min., the organic phase was washed with 1N aqueous HCI, with saturated bicarbonate solution and with saturated sodium chloride solution and dried over sodium sulfate. 10.2 g (100%) of 1-benzoylpiperidin-4-ylmethyl methanesulfonate were obtained as yellow crystals; m.p. 87°-90°.

Workup

  1. additionThen, 100 ml of 1N aqueous HCI were added
  2. stirringthe mixture was stirred for 5 min.
  3. washthe organic phase was washed with 1N aqueous HCI, with saturated bicarbonate solution and with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-ebcf76c1ed5f4339bb4bae6e7d47707b
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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