alpha-Naphthyl isocyanate → N-{4-[1-(Naphthylaminocarbonyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

HRID 1280767Notes

Reaction equation

HRID 1280767 reaction equation
[C:1]1([N:11]=[C:12]=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:34])[CH2:26][CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:16][CH2:15]1>C1COCC1>[C:1]1([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:34])[CH2:26][CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH2:16][CH2:15]2)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 18425707N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide

Product 1

HCID 18425749N-{4-[1-(Naphthylaminocarbonyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.6 g (17.7 mmol) 1-naphthyl isocyanate are dissolved in 15 ml abs. THF and cooled to 0° C. under moisture exclusion. 5.1 g (17.7 mmol) N-(4-piperidine-4-yl-butyl)-3-(pyridine-3-yl)-propionamide are dissolved in 35 ml abs. THF and added dropwise under ice cooling. The mixture is stirred without further cooling at RT overnight. Subsequently, the solution is drawn off under vacuum to a large extent and the residue is chromatographically purified over silica gel with CHCl3/CH3OH (90/10) and further purified by flash-chromatography with CHCl3/CH3OH (95/5 to 90/10). After drawing off the solvent, crystallization occurs from isopropanol/diisopropanol. Colorless crystals with a MP of 143-144° C. were recovered; yield 0.77 g (9%).

Workup

  1. customthe residue is chromatographically purified over silica gel with CHCl3/CH3OH (90/10)
  2. customfurther purified by flash-chromatography with CHCl3/CH3OH (95/5 to 90/10)
  3. customthe solvent, crystallization
  4. customColorless crystals with a MP of 143-144° C. were recovered

Sources & evidence

ORD record
ord-8a50a83f601a426286293639bc477a8b
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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