Pyridine → 1-[(4-Nitrophenyl)sulfonyl]piperidine

HRID 1984575

Reaction equation

HRID 1984575 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCCC1>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8082Piperidine

Product 1

HCID 7236241-[(4-Nitrophenyl)sulfonyl]piperidineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-nitrobenzenesulfonyl chloride 40 g 0.181 mole in dichloromethane 400 ml was added over 30 mins a solution of pyridine 15 g 15.3 ml and piperidine 16.15 g 18.8 ml in dichloromethane 100 ml. The mixture was stirred at room temperature for 2 h and then washed with water, 2M hydrochloric acid and brine, dried MgSO4 and evaporated in vacuo to give 1-(4-nitro-benzenesulfonyl)-piperidine 44.5 g. 1H NMR CDCl3 7.76 (2H, d), 7.40 (2H, d), 3.21 (6H, q), 1.07 (6H, t).

Workup

  1. washwashed with water, 2M hydrochloric acid and brine, dried MgSO4
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-a48dca5e4e0c4dfbaa748365c19e26a4
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Linked notes

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