HCID 18621467, compound → HCID 2235157, compound

HRID 1861765Notes

Reaction equation

HRID 1861765 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]=[N+]=[N-])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18621467HCID 18621467, compound

Product 1

HCID 2235157HCID 2235157, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-benzyl-1-(3-azidopropyl)piperidine (0.14 g, 0.54 mmol) in methanol (5 mL) was added Pd/C 5% (6 mg) and the resulting heterogeneous mixture was hydrogenated at 1 atm for 4 h. then filtered through a celite pad and concentrated in vacuum. The crude compound was purified by trituration with diethyl ether (5 mL) to give the title compound as a white solid (0.075g, 60%), mp 140-141° C. 1H-NMR (DMSO): 1.05-1.21 (m, 2H), 1.35-1.55 (m, 3H), 1.55-1.70 (m, 2H), 1.746 (t, J=11.1Hz, 2H), 2.281 (t, J=6.6Hz, 2H), 2.4-2.5 (m, 2H), 2.5-2.85 (m, 4H), 7.06-7.18 (m, 3H), 7.23 (t, J=7.2Hz, 2H), 7.8 (bs, 2H).

Workup

  1. filtrationthen filtered through a celite pad
  2. concentrationconcentrated in vacuum
  3. customThe crude compound was purified by trituration with diethyl ether (5 mL)

Sources & evidence

ORD record
ord-f2df8907d7a34681a25ebd7f335cec3e
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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