Acetic Acid → HCID 10338496, compound

HRID 2357507Notes

Reaction equation

HRID 2357507 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][N:8]([CH3:22])[C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C(O)(=O)C>ClCCCl>[CH3:7][N:8]([CH3:22])[C:9]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:11][CH:12]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 10338496HCID 10338496, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Piperidine (400 μl, 4 mmole) and 4-dimethylamino-4-phenylcyclohexanone (434 mg, 2 mmole) were dissolved in dry 1,2-dichloroethane (10 ml). Glacial acetic acid (2 mmole) and sodium triacetoxy boron hydride (600 mg, 2.8 mmole) were added to this mixture and the whole was stirred for 24 hours at RT. The reaction mixture was worked up by distilling off the 1,2-dichloroethane and the mixture was adjusted to pH 11 with 5M NaOH. The alkaline phase was diluted with water (10 ml) and extracted with EE (3×20 ml). The organic phase was dried with Na2SO4 and concentrated by evaporation. Dimethyl-(1-phenyl-4-piperidine-1-ylcyclohexyl)-amine was purified by chromatography with ethanol. The non-polar diastereoisomer (15 mg) still contained impurities, which also could not be removed by further purification attempts. The polar diastereoisomer was obtained as a colourless oil in a yield of 92 mg (16%).

Workup

  1. distillationby distilling off the 1,2-dichloroethane
  2. additionThe alkaline phase was diluted with water (10 ml)
  3. extractionextracted with EE (3×20 ml)
  4. dry with materialThe organic phase was dried with Na2SO4
  5. concentrationconcentrated by evaporation
  6. customDimethyl-(1-phenyl-4-piperidine-1-ylcyclohexyl)-amine was purified by chromatography with ethanol
  7. customThe non-polar diastereoisomer (15 mg) still contained impurities, which also could not be removed by further purification attempts
  8. customThe polar diastereoisomer was obtained as a colourless oil in a yield of 92 mg (16%)

Sources & evidence

ORD record
ord-c13ea23567f3438c92d6f48223f88122
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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