Acetic Acid → HCID 10367631, compound

HRID 2357434Notes

Reaction equation

HRID 2357434 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][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:4]2[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][CH2:3]2)=[CH:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 10367631HCID 10367631, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-piperidine-4-yl-1H-indole (200 mg, 1 mmole) and 4-dimethylamino-4-phenylcyclohexanone (217 mg, 1 mmole) were dissolved in dry 1,2-dichloroethane (20 ml). Glacial acetic acid (1 mmole) and sodium triacetoxy boron hydride (300 mg, 1.4 mmole) were added to this mixture. The reaction 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 (10 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 polar and the non-polar diastereoisomers were obtained in each case as a colourless oil in a yield of 90 mg (22%).

Workup

  1. distillationby distilling off the 1,2-dichloroethane
  2. additiondiluting 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. additiona mixture of two diastereoisomeric compounds, which
  7. customwere separated by chromatography with methanol
  8. customThe polar and the non-polar diastereoisomers were obtained in each case as a colourless oil in a yield of 90 mg (22%)

Sources & evidence

ORD record
ord-8f1c6c0082e7417384b797de75b4b187
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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