Triethylamine → 1-({[3-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-3-oxopropyl]amino}methyl)cyclohexanol

HRID 2383068Notes

Reaction equation

HRID 2383068 reaction equation
[C:1]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)(=[O:4])[CH:2]=[CH2:3].Cl.[NH2:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C>CC(O)C>[CH:15]1([CH:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][CH2:14][N:5]2[C:1](=[O:4])[CH2:2][CH2:3][NH:22][CH2:23][C:24]2([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 593966222-Acryloyl-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 251191601-({[3-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-3-oxopropyl]amino}methyl)cyclohexanolYield 28%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-acryloyl-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (516 mg) was dissolved in iPrOH (15 mL). To the reaction mixture were added 1-(aminomethyl)cyclohexanol hydrochloride (635 mg) and triethylamine (0.59 mL), followed by stirring under heating at reflux for 16 hours. Thereafter, the solvent was evaporated and water was added to the mixture, followed by extraction with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) and then further purified by alkaline silica gel column chromatography (chloroform) to obtain 1-({[3-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-3-oxopropyl]amino}methyl)cyclohexanol (214 mg).

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 16 hours
  3. customThereafter, the solvent was evaporated
  4. additionwater was added to the mixture
  5. extractionfollowed by extraction with chloroform
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)
  10. customfurther purified by alkaline silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-36a50cff17c54515ac3fff82e3d38b6f
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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