Water → 6-Methoxy-2-(methylethyl)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinoline

HRID 2114702Notes

Reaction equation

HRID 2114702 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=1)[N:8]([CH:21]([CH3:23])[CH3:22])[CH2:7][CH2:6]2.Cl.ClCC[N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[C:34](=[O:37])([O-])[O-].[K+].[K+].O.[CH3:41]N(C)C=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:37][CH2:34][CH2:41][CH:33]3[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]3)=[CH:18][CH:19]=1)[N:8]([CH:21]([CH3:22])[CH3:23])[CH2:7][CH2:6]2

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 234407376-Methoxy-2-(methylethyl)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 536880276-Methoxy-2-(methylethyl)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinolineYield 70%

Conditions

Temperature
80 °C

Procedure

A mixture of 6-methoxy-2-(methylethyl)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline (0.212 g, 0.68 mmol), 2-chloroethylpiperidine hydrochloride (0.25 g, 1.36 mmol), and potassium carbonate (0.47 g, 3.4 mmol) in dimethylformamide (10 mL) was heated at 80° C. overnight. After cooling to room temperature, the mixture was poured into water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 0-15% methanol/CH2Cl2) to provide the title compound (0.201 g, 70% yield): ES-MS (m/z) 423 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 0-15% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-3bdeb3d52b81484c9e49bf9c49832029
Source dataset
uspto-grants-2008_10
Patent number
US07435729B2

Reaction notes

Loading…