Potassium Carbonate → 5-chloro-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide

HRID 2294152Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20]2[N:30]=[CH:29][CH:28]=[CH:27][C:21]=2[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH2:12][CH2:11]1.[Cl:31]N1C(=O)CCC1=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:31][C:28]1[CH:29]=[N:30][C:20]([NH:19][CH2:18][CH2:17][CH2:16][N:13]2[CH2:12][CH2:11][N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[O:3][CH3:2])[CH2:15][CH2:14]2)=[C:21]([CH:27]=1)[C:22]([N:24]([CH3:26])[CH3:25])=[O:23]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide hydrochloride (0.287 g, 0.66 mmol), prepared as in Example 21, in 6 mL of DMF was heated to 50° C. and N-chlorosuccinimide (0.1 g, 0.73 mmol) was added. The mixture was stirred at 55° C. for 4 hours, diluted with water and basified with K2CO3 giving a precipitate. The precipitate was extracted with diethyl ether and the ether layer was washed twice with brine, dried (MgSO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with 5% methanol/methylene chloride to give 5-chloro-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide (0.188 g, 0.435 mmol) as an oil.

Workup

extractionThe precipitate was extracted with diethyl ether
washthe ether layer was washed twice with brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified on silica gel by column chromatography
washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record: ord-f3bd9bdff3364f5282d5bdd671fa9722
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688795

Reaction notes

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