Piperidine → Ethyl 2-methyl-4-piperidinobutyrate

HRID 441879

Reaction equation

HRID 441879 reaction equation
Br[CH2:2][CH2:3][CH:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C1C=CC=CC=1>[CH3:10][CH:4]([CH2:3][CH2:2][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12780980Ethyl 4-bromo-2-methylbutanoate

Product 1

HCID 20361120Ethyl 2-methyl-4-piperidinobutyrate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

10.5 g. (0.05 mole) of ethyl γ-bromo-α-methylbutyrate was combined with 17.0 g. (0.20 mole) of piperidine and 100 ml. of benzene and stirred for 16 hours at room temperature and heated at 60° C. for 4 hours. The reaction mixture was cooled and the colorless solid which appeared was removed by filtration. The mother liquor was concentrated to give ethyl α-methyl-γ-piperidinobutyrate as a mobile yellow liquid which distilled (b.p. 78° C. at 0.25 mm.) as 6.7 g. (63%) of colorless liquid. The nuclear magnetic resonance and infrared spectra were consistent with the desired compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe colorless solid which appeared was removed by filtration
  3. concentrationThe mother liquor was concentrated

Sources & evidence

ORD record
ord-5285d10f4538403f9ea38ebefec88d98
Source dataset
uspto-grants-1977_08
Patent number
US04042694

Linked notes

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