Potassium Carbonate → 2-[3-(4-Phenylpiperazin-1-yl)propylthio]benzylalcohol

HRID 1789371Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1.56 g of 2-(hydroxymethyl)thiophenol, 3.77 g of 1-(3-chloropropyl)-4-phenylpiperazine dihydrochloride, 5.02 g of potassium carbonate and 40 ml of dimethylformamide is stirred at 50° C. for 6 hours. Insoluble materials are filtered off, and the filtrate is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is digested with n-hexane and collected by filtration. 3.42 g of 2-[3-(4-phenylpiperazin-1-yl)propylthio]benzylalcohol are obtained. Yield: 91%.

Workup

filtrationInsoluble materials are filtered off
concentrationthe filtrate is concentrated under reduced pressure
customto remove solvent
additionWater is added to the residue
extractionthe aqueous mixture is extracted with ethyl acetate
washThe extract is washed with water
customdried
concentrationconcentrated under reduced pressure
customto remove solvent
filtrationcollected by filtration

Sources & evidence

ORD record: ord-55e7ad6b22ff44e29d699b8a2b766ad4
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689327

Reaction notes

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