4-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxymethyl]piperidine-1-carboxylic acid benzyl ester → 4-[4-Amino-3-(1-naphthylsulfonylmethyl)phenoxymethyl]piperidine-1-carboxylic acid benzyl ester

HRID 1711416Notes

Reaction equation

HRID 1711416 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[C:21]([CH2:28][S:29]([C:32]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH2:28][S:29]([C:32]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:20]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 588286324-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxymethyl]piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 588286244-[4-Amino-3-(1-naphthylsulfonylmethyl)phenoxymethyl]piperidine-1-carboxylic acid benzyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[3-(1-naphthylsulfonylmethyl)-4-nitrophenoxymethyl]-piperidine-1-carboxylic acid benzyl ester (0.9 g, 1.6 mmoles) and stannous chloride (1.8 g, 8 mmoles) in ethanol was heated at reflux temperature for 5 hours, cooled and concentrated under vacuum. The concentrate was diluted with water and extracted with EtOAc. The extracts were combined, dried over Na2SO4 and concentrated to afford the title compound (0.74 g, 1.36 mmoles).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 hours
  3. temperaturecooled
  4. concentrationconcentrated under vacuum
  5. additionThe concentrate was diluted with water
  6. extractionextracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a346c6d0801a427a8c86f14cd9bcccbc
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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