HCID 57874431, compound → HCID 57874485, compound

HRID 1093673Notes

Reaction equation

HRID 1093673 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:28])[CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-])=O)[CH2:14][CH2:13]2)=[O:11])=[CH:3][CH:2]=1>CO.[Pd]>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][CH:15]1[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][C:8]([NH:7][C:4]2[CH:5]=[CH:6][C:1]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:2][CH:3]=2)=[O:28])[CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 57874431HCID 57874431, compound

Product 1

HCID 57874485HCID 57874485, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-biphenyl-4-yl-3-[4-(2-nitro-phenoxy)-piperidin-1-yl]-3-oxo-propionamide (0.09 g, 0.00019 mole) in methanol (10 mL) was added 10% Pd/C (0.015 g) and the resulting mixture was stirred under an atmosphere of hydrogen for 30 minutes. The mixture was then filtered through celite, the celite was washed with methanol and the organic layers were concentrated under reduced pressure. The resulting residue was recrystallized from a mixture of hexane and chloroform to afford 0.025 g (29%) of 3-[4-(2-amino-phenoxy)-piperidin-1-yl]-N-biphenyl-4-yl-3-oxo-propionamide. LC-MS purity: 430.21 (M+1)+, 90.7%, 1H NMR (DMSO-d6): δ 7.7 (m, 6H), 7.4 (m, 2H), 7.3 (m, 1H), 6.8 (m, 1H), 6.6 (m, 2H), 6.5 (m, 1H), 4.6 (bs, 2H), 4.5 (bs, 1H), 3.8 (m, 2H), 3.5 (m, 4H), 2.0 (m, 2H), 1.8 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washthe celite was washed with methanol
  3. concentrationthe organic layers were concentrated under reduced pressure
  4. customThe resulting residue was recrystallized from a mixture of hexane and chloroform

Sources & evidence

ORD record
ord-3ef06eb8a4b84800a24efaefc0fb5cc5
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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