HCID 18621504, compound → HCID 22004648, compound

HRID 324532Notes

Reaction equation

HRID 324532 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([NH:21][NH:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][CH:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][CH2:12]2)=[O:32])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 18621504HCID 18621504, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22004648HCID 22004648, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(5-(4-benzylpiperidin-1-yl)valeroyl)-N′-(4-nitrobenzoyl)hydrazine (200 mg, 0.456 mmol) in 20 mL of methanol was added 50 mg of 5% Pd/C. The resulting mixture was hydrogenated at 30 psi of hydrogen for 3 hr. The catalyst was removed through a short column of Celite and was washed with methanol (15 mL). The extracts were evaporated in vacuo to give an oil, which was purified by flash chromatography to give the title product as a solid (60 mg, 32%):. mp 163-165° C.; 1H NMR (CDCl3) 1.26 (m, 2 H), 1.59 (m, 9 H), 1.92 (m, 2 H), 2.28 (m, 4 H), 2.52 (m, 2 H), 2.90 (m, 2 H), 3.29 (s, 2 H), 6.83 (d, J=8.1 Hz, 2 H), 7.10 (m, 3 H), 7.20 (m, 2 H), 7.63 (d, J=7.8 Hz, 2 H).

Workup

  1. customThe catalyst was removed through a short column of Celite
  2. washwas washed with methanol (15 mL)
  3. customThe extracts were evaporated in vacuo
  4. customto give an oil, which
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-4f96663a85784789962915c40e7ef52b
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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