Water → HCID 6516862, compound

HRID 1655667Notes

Reaction equation

HRID 1655667 reaction equation
Cl.[C:2]1([C:7]2([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH:3]=1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.O>C(O)C.[OH-].[Na+]>[ClH:18].[C:2]1([C:7]2([CH2:13][CH2:14][N:15]([CH3:16])[CH3:17])[CH2:11][CH2:10]/[C:9](=[CH:23]\[C:22]3[CH:25]=[CH:26][C:19]([Cl:18])=[CH:20][CH:21]=3)/[C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 19102975HCID 19102975, compound

Product 1

HCID 6516862HCID 6516862, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1.0 g (3.9 mmole) of 2-(1-cyclopenten-1-yl)-2-dimethylaminoethyl cyclopentanone hydrochloride and 8.1 mmole of 4-chloro-benzaldehyde in 40 ml of ethanol, 3.2 ml of 5N NaOH was added dropwise. The resulting mixture was stirred at about room temperature for about 12 hours and then mixed with 60 ml of water and extracted with ether. The ether extract was extracted with 6N HCl. The HCl extract was basified and extracted with ether, and then dried over anhydrous MgSO4. The ether solution was treated with ethanolic hydrogen chloride to give a precipitate, which was recrystallized from ethanol to give the 2-(1-Cyclopenten-1-yl)-2-dimethylaminoethyl-5-(E)-[(4-chloro) benzylidene] cyclopentanone hydrochloride. The melting point of the product was determined to be 234°-236° C.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. extractionwas extracted with 6N HCl
  4. extractionThe HCl extract
  5. extractionextracted with ether
  6. dry with materialdried over anhydrous MgSO4
  7. additionThe ether solution was treated with ethanolic hydrogen chloride
  8. customto give a precipitate, which
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-85352dd29ee947bfb3252dd205dfff21
Source dataset
uspto-grants-1993_10
Patent number
US05250735

Reaction notes

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