HCID 69450603, compound → HCID 69448963, compound

HRID 860166Notes

Reaction equation

HRID 860166 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:15]([CH3:19])[N:16]=[CH:17][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:15]([CH3:19])[N:16]=[CH:17][CH:18]=2)[CH2:12][CH2:13]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 69450603HCID 69450603, compound

Product 1

HCID 69448963HCID 69448963, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product of Step 1 (1.30 g, 4.9 mmol) and 20% Pd(OH)2 on carbon (600 mg) in MeOH (30 mL) was stirred at RT under an N2 atmosphere for 8 h. The mixture was filtered through a celite pad and the pad washed with MeOH (70 mL). To give after concentrating under reduced pressure, the piperidine (1.25 g, 96%). 1H NMR (CDCl3, 360 MHz) δ7.39 (1H, d, J=1.9 Hz), 6.00 (1H, d, J=1.9 Hz), 4.30–4.17 (2H, m), 3.83 (3H, s), 2.90–2.67 (3H, m), 1.95–1.81 (2H, m), 1.65–1.45 (2H, m), 1.48 (9H, s). MS (ES+) C14H23N3O2 requires: 265, found: 266 (M+H+, 65%).

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. washthe pad washed with MeOH (70 mL)
  3. customTo give
  4. concentrationafter concentrating under reduced pressure

Sources & evidence

ORD record
ord-33956c6f95fe41189028b0bf7bbb39a3
Source dataset
uspto-grants-2006_12
Patent number
US07153868B2

Reaction notes

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