HCID 22004675, compound → HCID 22004657, compound

HRID 324559Notes

Reaction equation

HRID 324559 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH:18]([OH:20])[CH3:19])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1)([O-])=O>CO.[Pd]>[ClH:1].[NH2:2][C:5]1[CH:22]=[CH:21][C:8]([CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH:18]([OH:20])[CH3:19])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 22004675HCID 22004675, compound

Product 1

HCID 22004657HCID 22004657, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-nitrobenzyl)-1-(3-hydroxy-butyl) piperidine hydrochloride (0.17 g, 0.53 mmol) in methanol (10 mL) with Pd/C, 10% (0.06 g) was hydrogenated at 1 atm and 25° C. for 18 h then, after filtration through a celite pad and concentration under reduced pressure, the crude compound was triturated with EtOAc (10 mL) for 15 h to afford the title compound (0.13 g, 80%) as a pale pink solid: mp 155-160° C.; 1H NMR (D2O) 1.038 (d, J=6.0, 3H), 1.28-1.36 (m, 2H), 1.58-1.82 (m, 5H), 2.342 (d, J=6.3, 2H), 2.65-2.80 (m, 2H), 2.90-3.10 (m, 2H), 3.32-3.43 (m, 2H), 3.65-3.80 (m, 1H), 6.64 (d, J=8.7, 2H), 6.909 (d, J=8.4, 2H); Anal calcd for C16H27ClN2OH2O: C, 60.65, H, 9.22, N, 8.84, found C, 61.45, H, 8.76, N, 8.81.

Workup

  1. filtrationafter filtration
  2. concentrationthrough a celite pad and concentration under reduced pressure
  3. customthe crude compound was triturated with EtOAc (10 mL) for 15 h

Sources & evidence

ORD record
ord-a7f31d995f2048ada3b09bec6e2a1223
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

Loading…