Water → HCID 22037886, compound

HRID 1790484Notes

Reaction equation

HRID 1790484 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[CH2:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28]Br)=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=4)[CH2:10][CH2:9][CH2:8]3)[CH2:5][CH2:6]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 22037933HCID 22037933, compound

Product 1

HCID 22037886HCID 22037886, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-piperidinyl)-7-methoxy-1,2,3,4-tetrahydroquinoline (250 mg), 2-(4-methoxyphenyl)ethyl bromide (260 mg) and diisopropylethylamine (270 mg) in DMF (5 ml) was heated at 60° C. for 12 hr under stirring. After the completion of the reaction, the reaction solution was cooled to room temperature and water was added thereto followed by extraction with ethyl acetate. The ethyl acetate layer was washed with brine and dried over magnesium sulfate. After evaporating the solvent, the resulting obtained residue was purified by silica gel column chromatography (toluene/acetone system) to give 1-{1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl}-7-methoxy-1,2,3,4-tetrahydroquinoline as an oil. This free compound was dissolved in ethyl acetate and 8.5% HCl/ethyl acetate was added thereto. The resulting hydrochloride was recrystallized from ethanol/ether to give the title compound (225 mg) (yield: 53%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthereto followed by extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe resulting obtained residue
  7. customwas purified by silica gel column chromatography (toluene/acetone system)

Sources & evidence

ORD record
ord-5c575ef3b5e34900bff568b0f0856dbc
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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