Ethanol → HCID 58653705, compound

HRID 1676038Notes

Reaction equation

HRID 1676038 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH:5]([NH:12][C:13]1[C:14]([N+:28]([O-])=O)=[C:15]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.NN.[CH2:35](O)C>[Ni]>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH:5]([N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]3)[C:14]=2[N:28]=[CH:35]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 58653686HCID 58653686, compound

Product 1

HCID 58653705HCID 58653705, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of 1-{3-[(3-methoxy-3-oxo-1-phenylpropyl)amino]-2-nitrophenyl}-4-piperidinecarboxylic acid (696 mg, 1.63 mmol) in ethanol (5 mL) was added Raney-Nickel (catalytic, ca. 5 mg) and hydrazine hydrate (316 μL, 6.52 mmol). The solution was stirred at room temperature for 3 hours, filtered, and evaporated in vacuo. The residue (560 mg) was dissolved in triethylorthoformate (5 mL), and heated at 60° C. for 0.5 hour. The resulting solution was cooled to room temperature, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (92:8) to afford the title compound, 1H NMR: (CD3OD) 8.27 (s, 1H), 7.34-7.28 (m, 5H), 7.10 (t, J=8.06, 1H), 6.99 (br d, J=8.06, 1H), 6.68 (d, J=8.06, 1H), 6.08 (dd, J=9.16, 6.22, 1H), 3.95-3.91 (m, 2H), 3.59 (obs dd, J=16.11, 9.16, 1H), 3.59 (s, 3H), 3.45 (dd, J=16.11, 6.22, 1H), 2.86-2.80 (m, 2H), 2.47-2.43 (m, 1H), 2.06-1.98 (m, 4H).

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. dissolutionThe residue (560 mg) was dissolved in triethylorthoformate (5 mL)
  4. temperatureheated at 60° C. for 0.5 hour
  5. temperatureThe resulting solution was cooled to room temperature
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with a mixture of dichloromethane and methanol (92:8)

Sources & evidence

ORD record
ord-6b6e8cf44ac04e94813f229243c06d6a
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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