Potassium Iodide → 3-Dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate

HRID 986709Notes

Reaction equation

HRID 986709 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH2:19][CH2:20][CH3:21])=[C:7]([CH:13]=[CH:14][C:15]=1[C:16](=[O:18])[CH3:17])[O:8][CH2:9][CH2:10][CH2:11]Br)(=[O:3])[CH3:2].Cl.[Br:23][C:24]1[CH:25]=[C:26]([CH:36]=[CH:37][C:38]=1[OH:39])[C:27]([O:29][CH2:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[O:28].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:4][C:5]1[C:6]([CH2:19][CH2:20][CH3:21])=[C:7]([CH:13]=[CH:14][C:15]=1[C:16](=[O:18])[CH3:17])[O:8][CH2:9][CH2:10][CH2:11][O:39][C:38]1[CH:37]=[CH:36][C:26]([C:27]([O:29][CH2:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[O:28])=[CH:25][C:24]=1[Br:23])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 201570243-(3-Acetoxy-4-acetyl-2-propylphenoxy)propylbromideHCID 201570253-Dimethylaminopropyl 3-bromo-4-hydroxybenzoate.hydrochloride

Product 1

HCID 137456293-Dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoateYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (30 ml), 3-(3-acetoxy-4-acetyl-2-propylphenoxy)propylbromide (1.6 g) was allowed to react with 3-dimethylaminopropyl 3-bromo-4-hydroxybenzoate.hydrochloride (1.7 g), potassium iodide (0.83 g) and potassium carbonate (0.7 g) at 60°-70° C. for 6 hours with stirring. Insoluble materials were filtered off, and the filtrate was concentrated. The resulting syrup was purified by means of a flash chromatography using silica-gel to give 3-dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate (1.8 g). The product was dissolved in ether, to which was added equivalent oxalic acid (250 mg) to give crystalline oxalate (1.8 g), m.p. 141°-142° C.

Workup

  1. filtrationInsoluble materials were filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe resulting syrup was purified by means of a flash chromatography

Sources & evidence

ORD record
ord-076e7e6f1da64693b75dc8f800036652
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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