Hydrochloric Acid → 8-[2,6-Dichloro-3-(piperazine-1-carbonyl)benzyloxy]-2-methylquinoline dihydrochloride

HRID 613649Notes

Reaction equation

HRID 613649 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]([Cl:36])=[C:18]([C:32]([Cl:35])=[CH:33][CH:34]=2)[CH2:19][O:20][C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]3)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:37]>C(OCC)(=O)C>[ClH:35].[ClH:37].[Cl:36][C:17]1[C:16]([C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:15])=[CH:34][CH:33]=[C:32]([Cl:35])[C:18]=1[CH2:19][O:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 183219658-[3-[4-(Tert-butoxycarbonyl)piperazine-1-carbonyl]-2,6-dichlorobenzyloxy]-2-methylquinoline

Product 1

HCID 183219628-[2,6-Dichloro-3-(piperazine-1-carbonyl)benzyloxy]-2-methylquinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-[3-[4-(tert-butoxycarbonyl)piperazine-1-carbonyl]-2,6-dichlorobenzyloxy]-2-methylquinoline (260 mg) and 4N solution of hydrogen chloride in ethyl acetate (2 ml) was stirred for 40 minutes at ambient temperature. The mixture was concentrated in vacuo, and the residue was crystallized from acetonitrile to give 8-[2,6-dichloro-3-(piperazine-1-carbonyl)benzyloxy]-2-methylquinoline dihydrochloride (227 mg) as pale yellow crystals.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-7c47cd9875614d0d8efc9d234cbfba3a
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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