HCID 178461285, compound → HCID 178461194, compound
Reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH2:4][CH2:3]1>O>[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH:8]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)[CH2:4][CH2:3]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
Ethyl polyphosphoric acid (10 mL) was added to trans-4-methyl-N-(2-phenylethyl)cyclohexanecarboxamide (2 g), followed by stirring under heating at 120° C. for 2 hours. Water was added to the reaction liquid which was then extracted with EtOAc. The organic layer was washed with water and saturated brine, and then dried over magnesium sulfate. The solvent was evaporated. To the resulting residue were added EtOH (10 mL) and then sodium borohydride (0.31 g) under ice-cooling, directly followed by stirring for 2 hours. Water was added to the reaction liquid, followed by extraction with EtOAc. The organic layer was washed with water and saturated brine, and then dried over magnesium sulfate. The solvent was evaporated to obtain 1-(trans-4-methylcyclohexyl)-1,2,3,4-tetrahydroisoquinoline (2 g).
Workup
- extractionwas then extracted with EtOAc
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
- additionTo the resulting residue were added EtOH (10 mL)
- temperaturesodium borohydride (0.31 g) under ice-cooling
- stirringby stirring for 2 hours
- additionWater was added to the reaction liquid
- extractionfollowed by extraction with EtOAc
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-d79874294c8e44b4b7c7d1e9ca8a8df6
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263607B2
Reaction notes
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