Dimethylamine → N,N-dimethylpiperidine-4-sulfonamide

HRID 734986Notes

Reaction equation

HRID 734986 reaction equation
[CH3:1][NH:2][CH3:3].[H-].[Na+].Cl[S:7]([CH:10]1[CH2:15][CH2:14][N:13](C(OCC2C=CC=CC=2)=O)[CH2:12][CH2:11]1)(=[O:9])=[O:8].O>CN(C)C=O>[CH3:1][N:2]([CH3:3])[S:7]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 24758Sodium hydrideHCID 21931260Benzyl 4-(chlorosulfonyl)piperidine-1-carboxylate

Product 1

HCID 46779214N,N-dimethylpiperidine-4-sulfonamideYield 133.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of an amine such as dimethylamine (4.72 mmol) and sodium hydride (4.72 mmol) in N,N-dimethylformamide (10 ml) was stirred for five minutes at room temperature. Then phenylmethyl 4-(chlorosulfonyl)-1-piperidinecarboxylate (1.60 mmol) was added to the reaction mixture and stirred at 100° C. for 3 hours. The reaction mixture was poured into water (25 ml) and extracted with ethyl acetate (3×25 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (410 mg, 80% yield) as an off-white solid. MS(ES)+ m/e 327.1 [M+H]+.

Workup

  1. stirringstirred at 100° C. for 3 hours
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26b17b507f674f7b811e61d47f6ef344
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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