Acetic Acid → {4-[3-(1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine

HRID 2357440Notes

Reaction equation

HRID 2357440 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1.[CH3:16][N:17]([CH3:31])[C:18]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.C(O)(=O)C>ClCCCl>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][N:1]([CH:21]3[CH2:20][CH2:19][C:18]([N:17]([CH3:31])[CH3:16])([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:23][CH2:22]3)[CH2:2]2)=[CH:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 153894433-(Piperidin-3-YL)-1H-indole

Product 1

HCID 57438232{4-[3-(1H-indol-3-yl)piperidine-1-yl]-1-phenylcyclohexyl}-dimethylamine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-piperidine-3-yl-1H-indole (233 mg, 1.16 mmole) and 4-dimethylamino-4-phenylcyclohexanone (253 mg, 1.16 mmole) were dissolved in dry 1,2-dichloroethane (20 ml). Glacial acetic acid (1.16 mmole) and sodium triacetoxy boron hydride (350 mg, 1.63 mmole) were added to this mixture. The mixture was then stirred for 24 hours at RT. The reaction mixture was worked up by distilling off the 1,2-dichloroethane and diluting with water (20 ml). The reaction mixture was adjusted to pH 11 with 5M NaOH and extracted with EE (3×20 ml). The organic phase was dried with Na2SO4 and concentrated by evaporation. The product was a mixture of two diastereoisomeric compounds, which were separated by chromatography with methanol. The non-polar diastereoisomer was obtained as a colourless oil in a yield of 208 mg (45%) and the polar diastereoisomer was obtained as a colourless oil in a yield of 50 mg (11%).

Workup

  1. distillationby distilling off the 1,2-dichloroethane
  2. additiondiluting with water (20 ml)
  3. extractionextracted with EE (3×20 ml)
  4. dry with materialThe organic phase was dried with Na2SO4
  5. concentrationconcentrated by evaporation
  6. additiona mixture of two diastereoisomeric compounds, which
  7. customwere separated by chromatography with methanol
  8. customThe non-polar diastereoisomer was obtained as a colourless oil in a yield of 208 mg (45%)
  9. customthe polar diastereoisomer was obtained as a colourless oil in a yield of 50 mg (11%)

Sources & evidence

ORD record
ord-b0b8cd98b82049339c83d2b61132263a
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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