2-Phenylcyclohexanone → HCID 68735476, compound

HRID 2382179Notes

Reaction equation

HRID 2382179 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C@@H:15]1[CH2:20][NH:19][CH2:18][CH2:17][NH:16]1.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[CH3:14][C@H:15]1[NH:16][CH2:17][CH2:18][N:19]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:20]1

Participants

6

Reactant 3

HCID 955922-PhenylcyclohexanoneHCID 4311764Sodium borohydrideHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 68735476HCID 68735476, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-phenylcyclohexanone (1.74 g, 9.99 mmol), (R)-2-methylpiperazine (3.00 g, 30.0 mmol) and titanium (4+) isopropoxide (5.85 ml, 20.0 mmol) was heated at 80° C. under N2 overnight. After cooling to rt, 10 mL of MeOH was added followed by slow addition of NaBH4 (1.13 g, 30.0 mmol). After stirring for 30 min, the solvent was evaporated and the residue was redissolved in EtOAc. The solution was treated with 15 g of NaHCO3 and 1 mL of water to generate slurry. This was filtered with large excess of EtOAc. The solvent was evaporated and the residue was submitted to flash chromatography (SiO2, DCM to DCM/MeOH=100:5 to 100:10 to 100:20) to give (3R)-3-methyl-1-(2-phenylcyclohexyl)-piperazine (1.82 g, 70.5% yield) as a colorless oil.

Workup

  1. temperatureAfter cooling to rt
  2. customthe solvent was evaporated
  3. dissolutionthe residue was redissolved in EtOAc
  4. additionThe solution was treated with 15 g of NaHCO3 and 1 mL of water
  5. filtrationThis was filtered with large excess of EtOAc
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bf74fe106e084fd6bdaaa33cb6d63f0b
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

Loading…