Dimethylformamide → HCID 12926022, compound

HRID 894624Notes

Reaction equation

HRID 894624 reaction equation
[OH:1][C:2]1[C:12]2[C:11](=[O:13])[C:8]3([CH2:10][CH2:9]3)[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][Cl:25])[CH3:21].CN(C)C=O>O>[ClH:25].[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][O:1][C:2]1[C:12]2[C:11](=[O:13])[C:8]3([CH2:9][CH2:10]3)[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chlorideHCID 12926017HCID 12926017, compound

Product 1

HCID 12926022HCID 12926022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxyspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one, (0.176 g.) potassium carbonate (0.276 g.), β-diethylaminoethyl chloride (0.215 g.) and N,N-dimethylformamide (5 ml.) was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried and distilled to remove the solvent. The residue was purified by column chromatography on silica gel, using chloroform as the eluent. The product was treated with HCl-saturated diethyl ether and the resultant hydrochloride was recrystallized from ethanol-diethyl ether. By the above procedure there was obtained 4-(2-diethylaminoethyloxy)spiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one hydrochloride as colorless needles, m.p. 160°-168° C. Yield 0.221 g.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by column chromatography on silica gel
  7. additionThe product was treated with HCl-saturated diethyl ether
  8. customthe resultant hydrochloride was recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-06e3c15783904fef939ca12a1d269103
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

Loading…