1-Benzyl-3-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxy]-piperidine → 4-(1-Benzylpiperidin-3-yloxy)-2-(1-naphthylsulfonylmethyl)phenylamine

HRID 1711421Notes

Reaction equation

HRID 1711421 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([CH2:24][S:25]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.CO.[Pd]>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([CH2:24][S:25]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:16]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 588286341-Benzyl-3-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxy]-piperidine

Product 1

HCID 588286234-(1-Benzylpiperidin-3-yloxy)-2-(1-naphthylsulfonylmethyl)phenylamineYield 88.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzyl-3-[3-(1-naphthylsulfonylmethyl)-4-nitro-phenoxy]-piperidine (1.2 g, 2.3 mmoles) and 10% Pd/C in THF and methanol was hydrogenated in a Parr hydrogenation bottle at 52 lb/in2 overnight. The reaction mixture was filtered through Celite, and the filtrate was concentrated under vacuum to afford the title compound as an off-white solid (1.0 g, 2.03 mmoles).

Workup

  1. customin2 overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-549894fdc961457184f2940a6a0d5865
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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