Dichloromethane → HCID 67717035, compound

HRID 1684585Notes

Reaction equation

HRID 1684585 reaction equation
[C:1]([C:4]1[C:5](CBr)=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[CH:11][C:10]([O:24][CH3:25])=[C:9]([O:26][CH3:27])[CH:8]=2)(=[O:3])[CH3:2].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.Cl[CH2:37]Cl>>[C:1]([C:4]1[C:5]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[C:11]([CH3:37])[C:10]([O:24][CH3:25])=[C:9]([O:26][CH3:27])[CH:8]=2)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8083MorpholineHCID 190399053-Acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline

Product 1

HCID 67717035HCID 67717035, compoundYield 72%

Procedure

A mixture of 3-acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (1.5 g), morpholine (1.42 g) and dichloromethane (30 ml) was stirred at room temperature for 15 hours. The reaction mixture was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform gave 3-acetyl-4-(3,4-dimethoxyphenyl)-2-morpholino-methyl-6,7-dimethoxyquinoline (1.1 g, 72%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 197°-199° C.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was evaporated
  4. washThe fractions eluted with chloroform

Sources & evidence

ORD record
ord-d1d6118993ea4a169ad48548d9a640a2
Source dataset
uspto-grants-1997_06
Patent number
US05641788

Reaction notes

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