1-Cyclohexene-1-carboxaldehyde → N-(cyclohexa-1-en-1-ylmethyl)-2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine

HRID 2383020Notes

Reaction equation

HRID 2383020 reaction equation
[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:17](=[O:20])[CH2:18][NH2:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21]1([CH:27]=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1>C(Cl)Cl.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[C:21]1([CH2:27][NH:19][CH2:18][C:17]([N:8]2[CH2:9][CH2:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:7]2[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:20])[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1

Participants

5

Reactant 2

HCID 51845401-Cyclohexene-1-carboxaldehydeHCID 593965892-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine

Product 1

HCID 67537633N-(cyclohexa-1-en-1-ylmethyl)-2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamineYield 62.6%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (695 mg) was dissolved in methylene chloride (12 mL), and titanium tetraisopropoxide (1.1 mL) and 1-cyclohexene-1-carboaldehyde (309 mg) were added thereto, followed by stirring at room temperature for 3 hours. Thereafter, the solvent was evaporated, and MeOH (15 mL) and then sodium cyanotrihydroborate (190 mg) were added to the mixture, followed by stirring for 14 hours. The solvent was evaporated, and water and EtOAc were added to the mixture. The mixture was filtered through celite and extracted with EtOAc. 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) to obtain N-(cyclohexa-1-en-1-ylmethyl)-2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (585 mg).

Workup

  1. customThereafter, the solvent was evaporated
  2. additionMeOH (15 mL) and then sodium cyanotrihydroborate (190 mg) were added to the mixture
  3. stirringby stirring for 14 hours
  4. customThe solvent was evaporated
  5. additionwater and EtOAc were added to the mixture
  6. filtrationThe mixture was filtered through celite
  7. extractionextracted with EtOAc
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-5cc4ff23798e42878d55fc5c46635a82
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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