Piperidine → HCID 22097603, compound

HRID 862652Notes

Reaction equation

HRID 862652 reaction equation
Br[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])=[C:11]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[C:10]2[C:5](=[CH:6][C:7]([O:31][CH3:32])=[C:8]([O:29][CH3:30])[CH:9]=2)[N:4]=1.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[CH3:30][O:29][C:8]1[CH:9]=[C:10]([C:11]2[C:19]3[C:24](=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[N:4]=[C:3]([CH2:2][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[C:12]=2[C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])[CH:5]=[CH:6][C:7]=1[O:31][CH3:32]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 15434504HCID 15434504, compound

Product 1

HCID 22097603HCID 22097603, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of propyl 2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (1.5 g), piperidine (1.27 g) and dichloromethane (30 ml) was stirred at room temperature for 2 days. The reaction mixture 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 (10/1, v/v) gave propyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperidinomethylquinoline-3-carboxylate (0.8 g, 53%) which was then recrystallized from ethyl acetate-hexane. Colorless prisms. mp. 129°-131° 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-ethyl acetate (10/1

Sources & evidence

ORD record
ord-0fd4f087915c47c680971e9e02522363
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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