Acetic Acid → HCID 57438248, compound

HRID 2357500Notes

Reaction equation

HRID 2357500 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=1.[CH3:18][N:19]([CH3:33])[C:20]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1.C(O)(=O)C>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[CH2:13][CH2:14][N:15]([CH:23]2[CH2:22][CH2:21][C:20]([N:19]([CH3:33])[CH3:18])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][CH2:24]2)[CH2:16][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1080295-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indoleHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 57438248HCID 57438248, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-methoxy-3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole (212 mg, 1.0 mmole) and 4-dimethylamino-4-phenylcyclo-hexanone (217 mg, 1.0 mmole) were dissolved in dry 1,2-dichloroethane (20 ml). Glacial acetic acid (1.0 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. The diastereoisomer mixture was obtained as a colourless solid in a yield of 343 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
  7. customThe diastereoisomer mixture was obtained as a colourless solid in a yield of 343 mg (80%)

Sources & evidence

ORD record
ord-3ccc6e1ecd1e412da7e8e12acd7e2424
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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