Piperidine → Ethyl 2-methyl-4-piperidinobutyrate

HRID 2398866Notes

Reaction equation

HRID 2398866 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 is combined with 17.0 g. (0.20 mole) of piperidine and 100 ml. of benzene, stirred for 16 hours at room temperature and heated at 60° C. for 4 hours. The reaction mixture is cooled and the colorless solid which appeared is removed by filtration. The mother liquor is concentrated to give ethyl α-methyl-γ-piperidinobutyrate as a mobile yellow liquid which distills (b.p. 78° at 0.25 mm.) as 6.7 g. (63%) of colorless liquid.

Workup

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

Sources & evidence

ORD record
ord-c002ded622fc4fad88d14b7b3562578c
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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