2-Naphthalenesulfonyl chloride → HCID 18425754, compound

HRID 1178403Notes

Reaction equation

HRID 1178403 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:3][CH2:2]1.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:3][CH2:2]1)(=[O:33])=[O:34]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 18425707N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide

Product 1

HCID 18425754HCID 18425754, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.5 g (12 mmol) N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide and 6.7 ml (48.1 mmol) TEA are placed in 100 ml absolute dichloromethane and cooled to ca 0° C. under moisture exclusion. 3.0 g (13.2 mmol) naphthalin-2-sulfonic acid chloride are dissolved in 40 ml absolute dichloromethane and added dropwise. The mixture is stirred without further cooling at RT overnight. Subsequently, the batch is washed twice, each with 80 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH (97/3) and crystallized from acetic acid ethyl ester after drawing off the solvent. Colorless crystals with an MP of 103-105° C.; yield 2.87 g (50%).

Workup

  1. temperaturecooled to ca 0° C. under moisture exclusion
  2. additionadded dropwise
  3. washSubsequently, the batch is washed twice
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed under vacuum
  6. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (97/3)
  7. customcrystallized from acetic acid ethyl ester

Sources & evidence

ORD record
ord-a52a2b244e314dcdb738d6e17e5f1301
Source dataset
uspto-grants-2007_10
Patent number
US07276524B2

Reaction notes

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