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Dimethylformamide → 1-(6-Bromo-4-quinolyl)-4-piperidyl methyl ether

HRID 1792437
Notes
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Reaction equation

HRID 1792437 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.Cl.[CH3:14][O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C.CN(C)C=O>O.C(OCC)(=O)C>[CH3:14][O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[N:8]=[CH:7][CH:6]=2)[CH2:18][CH2:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 51395376-Bromo-4-chloroquinolineHCID 115428134-Methoxypiperidine hydrochloride

Product 1

HCID 220321281-(6-Bromo-4-quinolyl)-4-piperidyl methyl etherYield 77.9%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 500 mg 6-bromo-4-chloroquinoline, 330 mg 4-methoxypiperidine monohydrochloride, 0.57 mL triethylamine and 10 mL N,N-dimethylformamide was stirred at 130° C. for 8 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and brine and dried over sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 516 mg of the title compound as a pale yellow oil.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-81d64fbcd2ec4401aa24fe933c90a8e1
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074801B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes