Chloroform → 4-amino-6,7-dimethoxy-2-[4-(N-phenylcarbamoyl)piperazin-1-yl]quinoline dihydrochloride

HRID 1788985Notes

Reaction equation

HRID 1788985 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[C:13]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:12]=1.C(Cl)(Cl)[Cl:32]>>[ClH:32].[ClH:32].[NH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[C:13]([N:25]2[CH2:26][CH2:27][N:28]([C:8](=[O:9])[NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:29][CH2:30]2)[CH:12]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 7672Phenyl isocyanateHCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

Product 1

HCID 201311314-amino-6,7-dimethoxy-2-[4-(N-phenylcarbamoyl)piperazin-1-yl]quinoline dihydrochloride

Procedure

Phenylisocyanate (1.1 g) was added to a stirred suspension of 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (0.72 g) in chloroform (25 ml) at room temperature and the reaction mixture was stirred for 4 hours. The mixture was evaporated in vacuo, the residue taken up in methanol-chloroform and treated with ethereal hydrogen chloride. The crude product was purified by chromatography on silica gel eluting with methylene chloride followed by chloroform/methanol and then recrystallised from methanol/ether to give 4-amino-6,7-dimethoxy-2-[4-(N-phenylcarbamoyl)piperazin-1-yl]quinoline dihydrochloride (0.18 g), m.p. 235°.

Workup

  1. customThe mixture was evaporated in vacuo
  2. additiontreated with ethereal hydrogen chloride
  3. customThe crude product was purified by chromatography on silica gel eluting with methylene chloride
  4. customrecrystallised from methanol/ether

Sources & evidence

ORD record
ord-198982f308634153beff07d8333f21f7
Source dataset
uspto-grants-1987_08
Patent number
US04686228

Reaction notes

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