Dichloromethane → N-(1-methyl-piperidin-4-yl)-4-nitro-benzenesulfonamide

HRID 2111415Notes

Reaction equation

HRID 2111415 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.C(N(C(C)C)C(C)C)C.ClCCl.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C(OCC)(=O)C>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][S:30]([C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:29][CH:28]=2)(=[O:31])=[O:32])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 22772515N-(1-methyl-piperidin-4-yl)-4-nitro-benzenesulfonamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.570 g (0.00477 mole) of 4-amino-1-methylpiperidine, 1.5 mL of ethyldiisopropylamine and 20 mL of dichloromethane at 0 degrees, was added 1.000 g (0.00451 mole) of 4-nitrobenzenesulfonyl chloride. The mixture was stirred for 1 hour and then diluted with 100 mL of ethyl acetate and washed successively twice with 20 mL of saturated sodium bicarbonate solution, twice with 20 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1.23 g of N-(1-methyl-piperidin-4-yl)-4-nitro-benzenesulfonamide as a yellow solid. The material was used without further purification.

Workup

  1. washwashed successively twice with 20 mL of saturated sodium bicarbonate solution, twice with 20 mL of brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8a11b5be3d04c02a8c6e21261e602c5
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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