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Ethanol → 4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2-piperidinomethylquinazoline

HRID 266138
Notes
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Reaction equation

HRID 266138 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([O:25][CH3:26])=[C:8]([O:23][CH3:24])[CH:9]=2)[N:4]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(O)C>ClCCl>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([C:11]2[C:10]3[C:5](=[CH:6][C:7]([O:25][CH3:26])=[C:8]([O:23][CH3:24])[CH:9]=3)[N:4]=[C:3]([CH2:2][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[N:12]=2)[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 107856562-Chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

Product 1

HCID 220976294-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2-piperidinomethylquinazolineYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (2.0 g), piperidine (2.27 g) and ethanol (40 ml)--dichloromethane (10 ml) was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and dichloromethane (50 ml) was added to the residue. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (1:1, v/v) gave 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperidinomethylquinazoline (1.46 g, 65%). This compound was recrystallized from ethyl acetate - hexane. Colorless needles, mp. 130°-132° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and dichloromethane (50 ml)
  2. additionwas added to the residue
  3. washThe dichloromethane layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe fractions eluted with chloroform-ethyl acetate (1:1

Sources & evidence

ORD record
ord-62b58b12b16246409ef872acfa573b56
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05650410

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes