Piperidine → 4-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]nitrobenzene

HRID 1071946Notes

Reaction equation

HRID 1071946 reaction equation
[O:1]1[CH2:17][CH:2]1[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)CC>[OH:1][CH:2]([CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 223906444-[N-(2,3-Epoxypropyl)sulphamoyl]nitrobenzene

Product 1

HCID 223906864-[N-(2-Hydroxy-3-piperidinopropyl)sulphamoyl]nitrobenzeneYield 90.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

4-[N-(2,3-Epoxypropyl)sulphamoyl]nitrobenzene (Method 116, 1 g, 3.88 mmol) and piperidine (0.34 g, 4 mmol) in 1-propanol (75 ml) were heated at reflux for 20 hours. The mixture was cooled and the solvent evaporated. The resulting yellow oil was triturated with diethyl ether collected by filtration and dried under vacuum to give the title compound 1.2 g (90%). NMR: 1.26-1.50 (m, 6H), 2.10-2.28 (m, 6H), 2.70 (dd, 1H), 2.90 (dd, 1H), 3.55 (m, 1H), 8.04 (d, 2H), 8.40 (d, 2H); m/z: 344.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent evaporated
  4. customThe resulting yellow oil was triturated with diethyl ether
  5. filtrationcollected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ef48e99a942248bc902a916f0bd4b137
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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