Carbon Dioxide → 2-[(4-Chlorophenyl)methyl]-1-methylpyrrolidine

HRID 1278028Notes

Reaction equation

HRID 1278028 reaction equation
C(OC([C:6](=[C:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=O)C.C(=O)=O.[OH-].[Na+]>Cl>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 54277062HCID 54277062, compound

Product 1

HCID 234525052-[(4-Chlorophenyl)methyl]-1-methylpyrrolidineYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Boil 40 g of 2-(α-ethoxycarbonyl-4-chlorobenzylidene)-1-methylpyrrolidine and 150 ml of conc. hydrochloric acid under reflux until the cessation of evolution of carbon dioxide. Cool the thus-obtained reaction mixture and then render it alkaline with 10% strength solution of sodium hydroxide before extracting the resulting product with 5×70 ml of diethyl ether. After drying over sodium sulfate, concentrate the ether extract to a solid residue. Hydrogenate the solid residue in 550 ml of ethanol with Pt/hydrogen to obtain 27.6 g of the title compound having a boiling point of 75° at 0.005 mm of Hg.

Workup

  1. temperatureCool
  2. customthe thus-obtained reaction mixture
  3. extractionbefore extracting the resulting product with 5×70 ml of diethyl ether
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationconcentrate the ether
  6. extractionextract to a solid residue

Sources & evidence

ORD record
ord-4ed7af0589a448cab782f918c6453b6c
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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