Sodium Hydroxide → 7-(1-Phenyl-3-dimethylaminopropoxy)-isoflavone

HRID 868545

Reaction equation

HRID 868545 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:20])[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][O:11]2)=[CH:6][CH:5]=1.Cl[CH:22]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C(Cl)Cl>[C:28]1([CH:22]([O:3][C:4]2[CH:13]=[C:12]3[C:7]([C:8](=[O:20])[C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:10][O:11]3)=[CH:6][CH:5]=2)[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 53768917-HydroxyisoflavoneHCID 127072393-Chloro-N,N-dimethyl-3-phenylpropan-1-amine

Product 1

HCID 129189147-(1-Phenyl-3-dimethylaminopropoxy)-isoflavone

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

200 ml of 50% aqueous sodium hydroxide solution and 1 g of triethylbenzylammonium chloride are added to a solution of 23.8 g of 7-hydroxyisoflavone in 100 ml of CH2Cl2, 20 g of 1-chloro-1-phenyl-3-dimethylaminopropane is added dropwise while stirring and stirring is continued for a further hour. Working up in the customary manner gives 7-(1-phenyl-3-dimethylaminopropoxy)-isoflavone. M.p. 128°-130°.

Workup

  1. additionis added dropwise
  2. stirringstirring
  3. waitis continued for a further hour

Sources & evidence

ORD record
ord-b0358f963c294462a6e573785cc0d55e
Source dataset
uspto-grants-1988_10
Patent number
US04780478

Linked notes

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