Benzaldehyde → HCID 19883697, compound

HRID 846712Notes

Reaction equation

HRID 846712 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O.C(OCC)(=O)C>[C:19]1(/[CH:18]=[CH:16]/[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:14][CH:13]=2)=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 19883666HCID 19883666, compound

Product 1

HCID 19883697HCID 19883697, compoundYield 81.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4 g of 4'-[3-(1-pyrrolidinyl)propyl]acetophenone and 2 g of benzaldehyde were dissolved in 80 ml of methanol and treated with a solution of 9.55 g of potassium carbonate in 38 ml of water within 15 minutes while cooling with an ice bath. The mixture was then left to react at room temperature for 18 hours and at about 40° for a further 18 hours. The reaction mixture was taken up in 200 ml of ethyl acetate and extracted with 100 ml of water. The aqueous phase was again extracted with 200 ml of ethyl acetate and the organic phases were again extracted with 100 ml of semi-saturated sodium chloride solution. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica gel with acetone. There were obtained 4.5 g (81%) of (E)-3-phenyl-4'-[3-(1-pyrrolidinyl)propyl]acrylophenone as a yellow oil; mass spectrum m/e: M+ 319 (7.1), 131 (1.4), 84 (100), 42 (7.5). For the formation of the hydrochloride, the free amine was dissolved in a small amount of ethanol and treated with 10M ethanolic hydrochloric acid solution. After recrystallization of the resulting material from isopropanol there was obtained the pure hydrochloride; m.p. 211°-213°.

Workup

  1. temperaturewhile cooling with an ice bath
  2. waitThe mixture was then left
  3. customto react at room temperature for 18 hours and at about 40° for a further 18 hours
  4. extractionextracted with 100 ml of water
  5. extractionThe aqueous phase was again extracted with 200 ml of ethyl acetate
  6. extractionthe organic phases were again extracted with 100 ml of semi-saturated sodium chloride solution
  7. dry with materialThe combined organic phases were dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel with acetone

Sources & evidence

ORD record
ord-23241d20ba1c44f2a2e55c7ba4f97d6c
Source dataset
uspto-grants-1992_08
Patent number
US05137920

Reaction notes

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