Ammonia → 3,3-Diphenyl-3,4,5,6-tetrahydropyridin-2-ol

HRID 2408824Notes

Reaction equation

HRID 2408824 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](OCC)=[O:7])#[N:2].N>CO.[Ni]>[C:11]1([C:5]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:4][CH2:3][CH2:1][NH:2][C:6]2=[O:7])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 67358715HCID 67358715, compound

Product 1

HCID 3211653,3-Diphenyl-3,4,5,6-tetrahydropyridin-2-ol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

The product of Example 1B (14.4 g, 49.1 mmol) and 7 M ammonia in methanol (150 mL) were added to solvent-washed Raney®-nickel (72.0 g, 1227 mmol), and the mixture was stirred at room temperature for 24 hours under hydrogen (30 pounds per square inch). The mixture was filtered through a nylon membrane, and the filtrate was concentrated. The residue was dissolved in dichloromethane/methanol (1:1) and filtered through diatomaceous earth to remove a greenish residue. The filtrate was concentrated to obtain a solid which was slurried in methanol, filtered, and dried to obtain the title compound. MS (DCI+) m/z 251 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane/methanol (1:1)
  4. filtrationfiltered through diatomaceous earth
  5. customto remove a greenish residue
  6. concentrationThe filtrate was concentrated
  7. customto obtain a solid which
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-23cfd9ecf1194a01b662a8800dcf4fde
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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