Dimethylformamide → HCID 12270328, compound

HRID 1579887Notes

Reaction equation

HRID 1579887 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.CN(C)[CH:14]=[O:15].N1([C:22]2[CH2:27][CH2:26]C[CH2:24][CH:23]=2)CCCC1>O>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7][CH:26]2[CH2:27][CH2:22][CH2:23][CH2:24][C:14]2=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 692722-Bromo-4'-methylacetophenoneHCID 707681-Pyrrolidino-1-cyclohexene

Product 1

HCID 12270328HCID 12270328, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 50 g. (0.23 mole) of p-methylphenacyl bromide in 120 ml. of dry dimethyl formamide was added dropwise during 1/2 hour into a stirred, cooled solution of 35.4 g. (0.23 mole) of 1-pyrrolidino-1-cyclohexene in 200 ml. of dimethyl formamide at a rate to maintain a temperature of 25°. After 51/2 hours, the solution was diluted with water and extracted with chloroform. The chloroform solution was washed with water, dried over sodium sulfate and concentrated to an oil. Distillation gave 28.5 g. (53%) of liquid, b.p. 161°-165° (0.2 mm.), which solidifed (m.p. 65°-70°).

Workup

  1. temperaturecooled solution of 35.4 g
  2. extractionextracted with chloroform
  3. washThe chloroform solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to an oil
  6. distillationDistillation
  7. customgave 28.5 g

Sources & evidence

ORD record
ord-31438979aa454b58bb14ae65fe8af055
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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