Hydrochloric Acid → HCID 20292477, compound

HRID 1390966Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]1.[CH:19]1[C:32]2[CH:31]([C:33]([Cl:35])=[O:34])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:24][C:23]=2[CH:22]=[CH:21][CH:20]=1.Cl>CC(C)=O>[ClH:35].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:33]([CH:31]2[C:32]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[O:24][C:25]3[C:30]2=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:34])[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3.8 g of 3-[4-(2-methoxyphenyl)-piperazin-1-yl]-1-hydroxy-propane in 40 ml of acetone is added dropwise at 20° C to a stirred solution of 4.9 g of xanthene-9-carbonyl chloride in 30 ml of acetone. The reaction mixture is refluxed for 30 minutes, allowed to cool to 60° C, and then ethanolic hydrochloric acid is added to the mixture until no more crystalline substance separates. The reaction mixture is cooled to 0° C, the separated crude substance is filtered off, and the crude substance is recrystallized from 20 ml of a 1:2 mixture of water and ethanol. 5.3 g (73%) of 3-[4-(2-methoxyphenyl)-piperazin-1-yl]-1-(xanthene-9-carbonyloxy)-propane hydrochloride are obtained; m.p.: 193°-195° C.

Workup

temperatureThe reaction mixture is refluxed for 30 minutes
temperatureThe reaction mixture is cooled to 0° C
customthe separated crude substance
filtrationis filtered off
customthe crude substance is recrystallized from 20 ml of a 1:2 mixture of water and ethanol

Sources & evidence

ORD record: ord-4bbe050d3d4c4926a9deeb1286c955c8
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04140790

Reaction notes

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