4-Piperidinecarboxamide → 1-(Naphthylsulfonyl)piperidine-4-carboxamide

HRID 2110831Notes

Reaction equation

HRID 2110831 reaction equation
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)=[O:3].C(N(CC)CC)C.[C:17]1([S:27](Cl)(=[O:29])=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>O1CCCC1>[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([S:27]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)(=[O:29])=[O:28])[CH2:6][CH2:5]1)=[O:3]

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 8471TriethylamineHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 239932921-(Naphthylsulfonyl)piperidine-4-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-aminocarbonylpiperidine (12.8 g, 100 mmol) in dry tetrahydrofuran (250 μL) containing triethylamine (20.2 g, 200 mmol) stirring at room temperature under argon, was added 1-naphthalenesulfonyl chloride (25 g, 110 mmol). After 16 h the solvent was evaporated under vacuum, and a solution of 25% methanol in diethyl ether (250 mL) was added to the residue. The resulting mixture was stirred for 2 h before the solid was filtered. The solid was washed with diethyl ether (50 mL twice), then water (50 mL twice), followed by diethyl ether (50 mL twice) again before drying under vacuum. This provided 4-aminocarbonyl-1-(1-naphthylsulfonyl)piperidine (27.9 g, 88% yield) as a white solid.

Workup

  1. customAfter 16 h the solvent was evaporated under vacuum
  2. additiona solution of 25% methanol in diethyl ether (250 mL) was added to the residue
  3. stirringThe resulting mixture was stirred for 2 h before the solid
  4. filtrationwas filtered
  5. washThe solid was washed with diethyl ether (50 mL twice), then water (50 mL twice),
  6. custombefore drying under vacuum

Sources & evidence

ORD record
ord-eca539380f3040539aafb91819d1a434
Source dataset
uspto-grants-2009_04
Patent number
US07517991B2

Reaction notes

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