Acetic Acid → HCID 10027773, compound

HRID 2357497Notes

Reaction equation

HRID 2357497 reaction equation
[NH:1]1[CH2:6][CH:5]=[C: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]([C:4]2[CH2:3][CH2:2][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)[CH2:6][CH:5]=2)=[CH:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 10027773HCID 10027773, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole (182 mg, 1 mmole) and 4-dimethylamino-4-phenylcyclohexanone (217 mg, 1 mmole) were dissolved in dry 1,2-dichloroethane (10 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 (4×20 ml). The organic phase was dried with Na2SO4 and concentrated by evaporation. The product was a mixture of two diastereoisomeric compounds, which could not be separated by chromatography. The diastereoisomer mixture was obtained as a colourless solid in a yield of 320 mg (80%).

Workup

  1. distillationby distilling off the 1,2-dichloroethane
  2. additiondiluting with water (10 ml)
  3. extractionextracted with EE (4×20 ml)
  4. dry with materialThe organic phase was dried with Na2SO4
  5. concentrationconcentrated by evaporation
  6. additiona mixture of two diastereoisomeric compounds, which could not
  7. custombe separated by chromatography
  8. customThe diastereoisomer mixture was obtained as a colourless solid in a yield of 320 mg (80%)

Sources & evidence

ORD record
ord-fc65587fbe7d44d7b0a2f4adf417b2bc
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

Loading…