Dimethylformamide → HCID 13504017, compound

HRID 35524Notes

Reaction equation

HRID 35524 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11](Cl)[CH:10](C)[C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17].[CH3:21]N(C)C=O>>[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:21][N:18]([CH2:19][CH3:20])[CH2:16][CH3:17])[CH2:10][C:9]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 679241251-Benzyl-4-chloro-methyl-pyrrolidin-2-one

Product 1

HCID 13504017HCID 13504017, compound

Procedure

A mixture of 14 g (0.06 mol) of crude 1-benzyl-4-chloro-methyl-pyrrolidin-2-one, prepared as in Example 1(a), 10 g of diethylamine and 50 ml of dimethylformamide was stirred or shaken for 2 hours at 150° C. in an autoclave. The reaction mixture was evaporated to dryness in vacuo, the residue was taken up in methylene chloride, and the solution was washed first with water and finally the title compound was extracted twice with 25 ml of 2 N HCl. The aqueous phase was separated, made alkaline with sodium hydroxide and the organic base was extracted with methylene chloride. The methylene chloride phase was evaporated, and the residue was distilled in vacuo.

Workup

  1. stirringshaken for 2 hours at 150° C. in an autoclave
  2. customThe reaction mixture was evaporated to dryness in vacuo
  3. washthe solution was washed first with water
  4. extractionfinally the title compound was extracted twice with 25 ml of 2 N HCl
  5. customThe aqueous phase was separated
  6. extractionthe organic base was extracted with methylene chloride
  7. customThe methylene chloride phase was evaporated
  8. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-4d7a621c68b44311af83ee1b5ed99db9
Source dataset
uspto-grants-1988_08
Patent number
US04767759

Reaction notes

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