Ethylenediamine → Tert-butyl 4-(benzylthio)-4-(nitromethyl)piperidine-1-carboxylate

HRID 453581Notes

Reaction equation

HRID 453581 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:15]([SH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[N+:23]([CH3:26])([O-:25])=[O:24].C(N)CN>C(#N)C>[CH2:15]([S:22][C:2]1([CH2:26][N+:23]([O-:25])=[O:24])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 57475998Tert-butyl 4-(benzylthio)-4-(nitromethyl)piperidine-1-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl 4-oxopiperidine-1-carboxylate (1.00 g), benzyl mercaptan (2.48 g), nitromethane (3.05 g), ethylenediamine (0.3 g) and acetonitrile (15 mL) was heated under reflux for 8 hr. The reaction solution was concentrated under, reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-3:1) to give the title compound (1.3 g, yield 71%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hr
  3. concentrationThe reaction solution was concentrated under, reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-3:1)

Sources & evidence

ORD record
ord-ca259569be474f4cb7e69d0d1a9390b1
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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