HCID 66712037, compound → HCID 66711636, compound

HRID 1262427Notes

Reaction equation

HRID 1262427 reaction equation
[C:1]([C:3]1([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]([NH2:12])=[O:11])[CH2:5][CH2:4]1)#[N:2]>[Pt].CO.C(Cl)Cl>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:3]2([C:1]#[N:2])[CH2:4][CH2:5][N:6]([CH2:9][C:10]([NH2:12])=[O:11])[CH2:7][CH2:8]2)=[CH:18][CH:17]=1

Participants

5

Reactant 1

HCID 66712037HCID 66712037, compound

Product 1

HCID 66711636HCID 66711636, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-[4-Cyano-4-(4-nitro-phenyl)-piperidin-1-yl]-acetamide (0.644 g, 2.23 mmol) was shaken over 5% Platinum on Carbon, Sulfided (0.5%) (94 mg, 0.024 mmol) in Methanol (10.0 mL) under an atmosphere of Hydrogen (40 psi) for 5 h. The precipitate was solubilized in DCM and then filtered to remove catalyst, washing with DCM. Conc. in vacuo to give 2-[4-(4-Amino-phenyl)-4-cyano-piperidin-1-yl]-acetamide (0.570 g; Yield=98.8) as an off white solid. 1H-NMR (DMSO-d6): 7.29 (s, 1H), 7.14 (m, 3H), 6.58 (d, 2H, J=8.4 Hz), 5.17 (s, 2H), 3.17 (d, 1H, J=5.2 Hz), 2.92 (s, 2H), 2.90 (m, 2H), 2.39 (m, 2H), 2.00 (m, 4H).

Workup

  1. filtrationfiltered
  2. customto remove catalyst
  3. washwashing with DCM

Sources & evidence

ORD record
ord-a2128180dbb74063863d4ee7bddb0b41
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…