Ethanol → HCID 5387760, compound

HRID 1655661Notes

Reaction equation

HRID 1655661 reaction equation
[ClH:1].[CH3:2][NH:3][CH3:4].C=O.[CH2:7](O)C.[CH2:10]([O:12][C:13]([CH2:15][O:16][C:17]1[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=1/[CH:19]=[C:20]1/[C:21](=[O:25])[CH2:22][CH2:23][CH2:24]/1)=[O:14])[CH3:11]>Cl.O>[ClH:1].[CH3:2][N:3]([CH2:7][CH:22]1[CH2:23][CH2:24]/[C:20](=[CH:19]\[C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[O:16][CH2:15][C:13]([O:12][CH2:10][CH3:11])=[O:14])/[C:21]1=[O:25])[CH3:4]

Participants

7

Reactant 4

HCID 702EthanolHCID 712Formaldehyde2×HCID 10473Dimethylamine, hydrochlorideHCID 67821679HCID 67821679, compound

Product 1

HCID 5387760HCID 5387760, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

2.0 g of dimethylamine hydrochloride, 1.8 g of paraformaldehyde and 30 ml of ethanol were added with 3 drops of concentrated hydrochloric acid to 6.5 g of 2-(E)-(2-ethoxycarbonylmethoxylbenzylidene) cyclopentanone. After refluxing for about 2 hours, the resulting solution was treated with 0.7 g of paraformaldehyde and then refluxed for about 2 additional hours. After the solvent was removed in vacuo, a syrupy residue was obtained. Then 100 ml of water was added to the residue, stirred for about 10 minutes, and filtered. The filtrate was adjusted to about pH 9 by the addition of 10% sodium carbonate solution and extracted with three 20 ml portions of ether. The aqueous layer was again treated with 10% sodium carbonate solution to about pH 11 and extracted with two additional 20 ml portions of ether. The combined ether was dried over anhydrous magnesium sulfate and treated with ethanolic hydrogen chloride. It was filtered to give 4.7 g of product Recrystallization from absolute ethanol-acetone gave 4.2 g of 2-Dimethylaminomethyl-5-(E)-(2-ethoxycarbonylmethoxyl-benzylidene) cyclopentanone hydrochloride as a white powder product. The melting point of the product was determined to be 124°-126° C.

Workup

  1. temperatureAfter refluxing for about 2 hours
  2. temperaturerefluxed for about 2 additional hours
  3. customAfter the solvent was removed in vacuo
  4. customa syrupy residue was obtained
  5. filtrationfiltered
  6. additionThe filtrate was adjusted to about pH 9 by the addition of 10% sodium carbonate solution
  7. extractionextracted with three 20 ml portions of ether
  8. additionThe aqueous layer was again treated with 10% sodium carbonate solution to about pH 11
  9. extractionextracted with two additional 20 ml portions of ether
  10. dry with materialThe combined ether was dried over anhydrous magnesium sulfate
  11. additiontreated with ethanolic hydrogen chloride
  12. filtrationIt was filtered
  13. customto give
  14. custom4.7 g of product Recrystallization from absolute ethanol-acetone

Sources & evidence

ORD record
ord-76edc171e5954187bb8cb5a7ae95022f
Source dataset
uspto-grants-1993_10
Patent number
US05250735

Reaction notes

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