Potassium Carbonate → 2,2,2-Trichloroethyl 4-[4-(hydroxymethyl)piperidin-1-yl]butanoate

HRID 1172272Notes

Reaction equation

HRID 1172272 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20]>CC(C)=O>[Cl:24][C:23]([Cl:25])([Cl:26])[CH2:22][O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4207714-PiperidinemethanolHCID 111200754-Bromobutyric acid, 2,2,2-trichloroethyl ester

Product 1

HCID 574299132,2,2-Trichloroethyl 4-[4-(hydroxymethyl)piperidin-1-yl]butanoateYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 4-piperidinemethanol (1.72 g, 15.0 mmol) in acetone (100 ml) was added K2CO3 (4.14 g, 30. mmol) and 2,2,2-trichloroethyl 4-bromobutyrate (4.47 g, 15.0 mmol) and heated under reflux for 3 h. The reaction mixture was cooled to room temperature, filtered and the filtrate concentrated in vacuo. The residue was added CH2Cl2 (75 ml) and washed with brine (25 ml) and H2O (2×25 ml). The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to leave the title compound as a viscous oil (4.70 g, 94.1%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. additionThe residue was added CH2Cl2 (75 ml)
  6. washwashed with brine (25 ml) and H2O (2×25 ml)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-a4c98270f4324aedab288cdaf5d7be23
Source dataset
uspto-grants-2010_11
Patent number
US07834010B2

Reaction notes

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