Pyrrolidine → 1,2,3,6-Tetrahydro-3-methyl-4-pyrrolidinylpyridine-1-carboxylic acid ethyl ester

HRID 444195

Reaction equation

HRID 444195 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][C:9](=O)[CH:8]([CH3:13])[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>C1C=CC=CC=1>[CH2:4]([O:3][C:1]([N:6]1[CH2:11][CH:10]=[C:9]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:8]([CH3:13])[CH2:7]1)=[O:2])[CH3:5]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 15075657Ethyl 3-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 572594601,2,3,6-Tetrahydro-3-methyl-4-pyrrolidinylpyridine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 92.2 g of 1-carbethoxy-3-methyl-4-piperidone and 53.5 g of pyrrolidine in 1.0 liter of benzene is heated to the boil at reflux for 2 hours and the resulting water is continuously removed azeotropically. The reaction mixture is concentrated and the crude 1,2,3,6-tetrahydro-3-methyl-4-pyrrolidinylpyridine-1-carboxylic acid ethyl ester, obtained as an oil, is used as such for the next reaction.

Workup

  1. temperatureis heated to the boil
  2. temperatureat reflux for 2 hours
  3. customthe resulting water is continuously removed azeotropically
  4. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-f2a9b5ec26064b169af90b9d44521f4d
Source dataset
uspto-grants-1981_04
Patent number
US04263298

Linked notes

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