Methanesulfonyl chloride → Methanesulfonic acid 2,2-dimethyl-3-piperidin-1-yl-propyl ester

HRID 1867443

Reaction equation

HRID 1867443 reaction equation
[CH3:1][C:2]([CH3:12])([CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][OH:4].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>ClCCl>[CH3:1][C:2]([CH3:12])([CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][O:4][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2960142,2-Dimethyl-3-(piperidin-1-yl)propan-1-ol

Product 1

HCID 86615874Methanesulfonic acid 2,2-dimethyl-3-piperidin-1-yl-propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.51 g (2.99 mmol) of 2,2-dimethyl-3-piperidin-1-yl-propan-1-ol in 7 ml of dichloromethane was treated at 0° C. with 0.24 ml (179.59 mmol) of methanesulfonyl chloride and stirred at RT for 2.5 h. The reaction was extracted with aqueous saturated NaHCO3 /Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, dried over Na2SO4 and evaporated to give 0.85 g (quantitative) of the title compound as light brown oil. MS: 249.2 (M+).

Workup

  1. extractionThe reaction was extracted with aqueous saturated NaHCO3 /Et2O (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-b8f14f3b593a4cca8fcdebf26c3f20bc
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Linked notes

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