Hydrochloric Acid → 2-{3-[4-(5-chloro-2-methoxyphenyl)-piperazin-1-yl]propylamino}-N,N-dimethylbenzamide hydrochloride

HRID 2294149Notes

Reaction equation

HRID 2294149 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]3[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=3[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH2:10][CH2:9]2)[CH:7]=1.Cl.CCOCC>CO.C(Cl)Cl.CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]3[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=3[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH2:12][CH2:13]2)[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 214734652-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl-amino}-N,N-dimethylbenzamide

Product 1

HCID 214734712-{3-[4-(5-chloro-2-methoxyphenyl)-piperazin-1-yl]propylamino}-N,N-dimethylbenzamide hydrochlorideYield 186.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 2-{3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl-amino}-N,N-dimethylbenzamide (265 mg, 0.61 mmol) in 0.4 mL of 5% methanol/methylene chloride was acidified with 2 mL of 1M hydrochloric acid in methanol and then ether was added to give a precipitate. The supernatant was decanted and the precipitate was washed with ether, collected and dried to give 2-{3-[4-(5-chloro-2-methoxyphenyl)-piperazin-1-yl]propylamino}-N,N-dimethylbenzamide hydrochloride (270 mg, 0.57 mmol), m.p. 90°-135° C. Anal.: Calcd. for C23H31ClN4O2.HCl.(H2 O)0.5 : C, 57.98; H, 6.98; N, 11.76%; Found: C, 57.79H, 6.80; N, 11.72%.

Workup

  1. customto give a precipitate
  2. customThe supernatant was decanted
  3. washthe precipitate was washed with ether
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-72d84c643b4d4630810b20b6572d8612
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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