Acetic Acid → HCID 57438247, compound

HRID 2357494Notes

Reaction equation

HRID 2357494 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.[CH3:17][N:18]([CH3:32])[C:19]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.C(O)(=O)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH:22]2[CH2:21][CH2:20][C:19]([N:18]([CH3:32])[CH3:17])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:24][CH2:23]2)[CH2:15][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 57438247HCID 57438247, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-chloro-3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole (170 mg, 0.79 mmole) and 4-dimethylamino-4-phenylcyclohexanone (171 mg, 0.79 mmole) were dissolved in dry 1,2-dichloro-ethane (10 ml). Glacial acetic acid (0.79 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 diastereoisomer mixture was obtained as a colourless solid in a yield of 340 mg (100%).

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. customThe diastereoisomer mixture was obtained as a colourless solid in a yield of 340 mg (100%)

Sources & evidence

ORD record
ord-572aa9cabb6e46eea686b53c2ec40eee
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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