4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester

HRID 2113465Notes

Reaction equation

HRID 2113465 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][OH:9])[CH2:3]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.CCN(CC)CC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][O:9][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:3]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 97998(1-Methyl-3-piperidyl)methanol

Product 1

HCID 21184160Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl esterYield 99.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.07 g (16 mmol) 1-methyl-3-piperidinemethanol, 3.35 g (18 mmol) p-toluensulfonyl chloride, 0.58 g (5 mmol) 4-dimethylaminopyridine and 2.23 mL (16 mmol) NEt3 in 30 mL DCM was stirred for 2 h at room temperature. The mixture was washed with water and evaporated to dryness to yield 4.5 g (99%) of the title compound as yellow oil which was used without further purification. MS(m/e): 284.1 (MH+).

Workup

  1. washThe mixture was washed with water
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-45b36af8ebb04e54917a3573e8436744
Source dataset
uspto-grants-2008_10
Patent number
US07432255B2

Reaction notes

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