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

HRID 2267704Notes

Reaction equation

HRID 2267704 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-d0cf871d6c214b2f86315dba9fdb95b4
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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