Benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate → N,N-dimethylpiperidine-4-sulfonamide

HRID 734987Notes

Reaction equation

HRID 734987 reaction equation
[CH3:1][N:2]([CH3:22])[S:3]([CH:6]1[CH2:11][CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[CH2:8][CH2:7]1)(=[O:5])=[O:4].[H][H]>CO.[Pd]>[CH3:1][N:2]([CH3:22])[S:3]([CH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 53587548Benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 46779214N,N-dimethylpiperidine-4-sulfonamideYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of phenylmethyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate (1.19 mmol) and 10% wt palladium/carbon (0.09 mmol) in methanol (10 ml) was vacuum pumped and back-filled with nitrogen three times. The nitrogen atmosphere was then replaced with hydrogen via a balloon and the reaction stirred for 1 hour at ambient temperature. The reaction was then filtered through a pad of celite and concentrated to give the title compound (200 mg, 87% yield), which was used directly in the next reaction without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.33 (bs, 1H) 3.30-3.22 (m, 1H) 2.96 (d, J=12.13, 2H) 2.84 (s, 6H) 2.46 (td, J=2.53, 12.38, 2H) 1.80 (d, J=12.13, 2H) 1.46 (qt, J=4.17, 12.34, 2H)

Workup

  1. additionback-filled with nitrogen three times
  2. filtrationThe reaction was then filtered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-87461cb28dec424ead1127c70d2291fa
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

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