4-Piperidinecarboxylic acid → 1-(2-Naphthylsulfonyl)-4-piperidinecarboxylic acid

HRID 843692Notes

Reaction equation

HRID 843692 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[S:20]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)(=[O:21])=[O:22]

Participants

4

Reactant 2

HCID 37734-Piperidinecarboxylic acidHCID 71252-Naphthalenesulfonyl chloride

Product 1

HCID 8118441-(2-Naphthylsulfonyl)-4-piperidinecarboxylic acidYield 75.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

26.0 g (0.2 mol) of piperidine-4-carboxylic acid were dissolved in 250 ml of pyridine and the solution was treated with 47.6 g (0.2 mol) of 2-naphthylsulfonyl chloride in portions at room temperature. The whole was stirred at room temperature for about 5 h. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and 2 M hydrochloric acid. The organic phase was dried and concentrated under reduced pressure. 48.5 g (75%) of the product were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and 2 M hydrochloric acid
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52ed6fcefbb44c5d97d8649eef1cb4ee
Source dataset
uspto-grants-2002_04
Patent number
US06380220B1

Reaction notes

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