2-Naphthalenesulfonyl chloride → HCID 3852743, compound

HRID 499256Notes

Reaction equation

HRID 499256 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 100867Ethyl 4-amino-1-piperidinecarboxylate

Product 1

HCID 3852743HCID 3852743, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

TEA (0.088 mol, 12.4 ml) was added at 10° C. to a solution of 4-amino-1-piperidinecarboxylic acid, ethyl ester (0.044 mol, 7.6 g) in DCM (110 ml) under N2 flow. A solution of 2-naphtalenesulfonyl chloride (0.044 mol) in DCM (50 ml) was added dropwise. The mixture was stirred at 10° C. for 1 hour and 30 minutes, poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was taken up in diethylether, the precipitate was filtered and dried yielding 13.8 g of 4-[(2-naphthalenylsulfonyl)amino]-1-piperidinecarboxylic acid, ethyl ester, melting point 128° C., intermediate 1.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. filtrationthe precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-9263df8dc9144546a04f7c8713aea0a6
Source dataset
uspto-grants-2010_08
Patent number
US07767679B2

Reaction notes

Loading…