Khellinone → 5-Acetyl-4,7-dimethoxy-6-[3-((2-(3,4-dimethoxyphenyl)-ethyl)-methylamino)propoxy]-benzofuran

HRID 2248375Notes

Reaction equation

HRID 2248375 reaction equation
[C:1]([C:4]1[C:5]([OH:17])=[C:6]([O:15][CH3:16])[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2].Cl[CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1)[CH3:23]>C(C(C)=O)C>[C:1]([C:4]1[C:5]([O:17][CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[CH3:23])=[C:6]([O:15][CH3:16])[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 68086KhellinoneHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamine

Product 1

HCID 144216745-Acetyl-4,7-dimethoxy-6-[3-((2-(3,4-dimethoxyphenyl)-ethyl)-methylamino)propoxy]-benzofuran

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

39 g of 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran are refluxed with 40 g of 3-chloropropyl-(2-(3,4-dimethoxyphenyl)-ethyl)-methylamine in 250 ml of methyl ethyl ketone for 14 hours. The mixture is filtered, the solvent is stripped off and the oily residue is dissolved in dilute HCl. The aqueous phase is washed with ether, rendered alkaline with dilute sodium hydroxide solution and extracted with ether. Stripping off the solvent gives 45 g of crude oily product which is further reacted without purification.

Workup

  1. filtrationThe mixture is filtered
  2. dissolutionthe oily residue is dissolved in dilute HCl
  3. washThe aqueous phase is washed with ether
  4. extractionextracted with ether
  5. customgives 45 g of crude oily product which
  6. customis further reacted without purification

Sources & evidence

ORD record
ord-97959657207b47fda9153348633742fb
Source dataset
uspto-grants-1991_08
Patent number
US05039701

Reaction notes

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