Triethylamine → 2,2-Dimethyl-propionic acid 1-benzyl-piperidin-4-yl ester

HRID 1929004Notes

Reaction equation

HRID 1929004 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:24](=[O:25])[C:23]([CH3:28])([CH3:27])[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 668415652,2-Dimethyl-propionic acid 1-benzyl-piperidin-4-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-piperidin-4-ol (25 g, 130.7 mmol) and triethylamine (36.1 ml, 261.4 mmol) in 250 ml of THF is treated with 2,2-dimethyl-propionyl chloride (32.2 ml, 261.4 mmol). The suspension is heated under reflux over night. The solvent is evaporated, the residue taken up in DCM and washed with saturated sodium bicarbonate solution and brine. Drying and evaporation gave an orange oil.

Workup

  1. temperatureThe suspension is heated
  2. temperatureunder reflux over night
  3. customThe solvent is evaporated
  4. washwashed with saturated sodium bicarbonate solution and brine
  5. customDrying
  6. customevaporation
  7. customgave an orange oil

Sources & evidence

ORD record
ord-c642426ec3d7457a964172b978c36934
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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