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

HRID 1366823

Reaction equation

HRID 1366823 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. 1HNMR 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-a37ef5898cf1416d9d61c31bfd1f2d7b
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Linked notes

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