4-Hydroxybenzaldehyde → Benzaldehyde, 4-(3-(4-phenyl-1-piperazinyl)propoxy)-

HRID 375533Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.Cl[CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17]1>CN(C)C=O>[C:22]1([N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][O:3][C:4]3[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=3)[CH2:21][CH2:20]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (3.59 g of 60% in oil) is added to 4-hydroxybenzaldehyde (9.95 g) in dimethylformamide (250 mL) and the mixture stirred at 60° C. for 30 minutes. 1-(3-Chloropropyl)-4-phenylpiperazine (Step A) (19.5 g) is added and the mixture stirred for 14 hours at 60° C. The solvent is evaporated and the residue treated with water (300 mL) and extracted with dichloromethane (3×150 mL). The extracts are dried over magnesium sulfate, filtered and evaporated to leave a beige solid. This solid is recrystallized from ethyl acetate/diethyl ether to give 18.4 g of the title compound as a light beige solid.

Workup

stirringthe mixture stirred for 14 hours at 60° C
customThe solvent is evaporated
additionthe residue treated with water (300 mL)
extractionextracted with dichloromethane (3×150 mL)
dry with materialThe extracts are dried over magnesium sulfate
filtrationfiltered
customevaporated
customto leave a beige solid
customThis solid is recrystallized from ethyl acetate/diethyl ether

Sources & evidence

ORD record: ord-0498d120f60344b48fdaa4502b8c9272
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486517

Reaction notes

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