2-Naphthalenesulfonyl chloride → HCID 18425754, compound

HRID 1280766Notes

Reaction equation

HRID 1280766 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 g (48.1 mmol) TEA are present in 100 ml abs. dichloromethane and cooled to ca. 0° C. under moisture exclusion. 3.0 g (13.2 mmol) naphthaline-2-sulfonic acid chloride are dissolved in 40 ml abs 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 a MP of 103-105° C. were recovered; yield: 2.87 g (50%).

Workup

  1. additionadded dropwise
  2. washSubsequently, the batch is washed twice
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent is removed under vacuum
  5. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (97/3)
  6. customcrystallized from acetic acid ethyl ester
  7. customColorless crystals with a MP of 103-105° C. were recovered

Sources & evidence

ORD record
ord-4c3175e8695f4587a13af114a4f2d96f
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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