Water → Hydrochloric Acid

HRID 2259904Notes

Reaction equation

[CH3:1][N:2]([CH2:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][Cl:5].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[ClH:5].[ClH:5].[CH3:1][N:2]([CH2:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][N:36]1[CH2:35][CH2:34][N:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH3:25])[CH2:38][CH2:37]1.[ClH:5]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5.2 g of Intermediate XXVII, 3.1 g of 1-(2-methoxyphenyl)-piperazine and 2.2 g of anhydrous potassium carbonate in 50 ml of dimethylformamide was stirred at 70° C. for 7 hours. After cooling to 20°-25° C., the reaction mixture was poured into 500 ml of water, and extracted with dichloromethane. The organic phase was washed with water and dried on anhydrous sodium sulfate. The solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate:petroleum ether (98:2). The title compound was obtained by salification with ethanolic hydrogen chloride. m.p. 217°-219=C.

Workup

temperatureAfter cooling to 20°-25° C.
extractionextracted with dichloromethane
washThe organic phase was washed with water
dry with materialdried on anhydrous sodium sulfate
customThe solvent was removed in vacuo
customThe residue was purified by flash chromatography on silica gel
washeluting with ethyl acetate:petroleum ether (98:2)

Sources & evidence

ORD record: ord-f83826f987f9488a90df69f086d95b99
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05474994

Reaction notes

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