Sodium Hydroxide → N-{4-[1-(2-naphthoyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

HRID 1280768Notes

Reaction equation

HRID 1280768 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[C:32](Cl)=[O:33].[OH-].[Na+]>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[C: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]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 752462-Naphthoyl chlorideHCID 18425707N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide

Product 1

HCID 18425752N-{4-[1-(2-naphthoyl)-piperidin-4-yl]-butyl}-3-(pyridin-3-yl)-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.0 g (20.7 mmol) N-(4-piperidine-4-yl-butyl)-3-(pyridine-3-yl)-propionamide and 2.1 g (20.7 mmol) TEA are dissolved in 30 ml abs. dichloromethane and cooled to ca. 0° C. under moisture extraction. 3.95 g (20.7 mmol) 2-naphthoylchloride are dissolved in 40 ml abs. dichloromethane and added dropwise under ice cooling. The mixture is stirred without further cooling at RT overnight. Subsequently, the batch is made basic by the addition of 10% sodium hydroxide solution and washed twice with a small amount of water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The resinous residue is chromatographically purified with CHCl3/CH3OH (96/4). Yield of colorless resin: 5.4 g (59%).

Workup

  1. washwashed twice with a small amount of water
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe solvent is removed under vacuum
  4. customThe resinous residue is chromatographically purified with CHCl3/CH3OH (96/4)

Sources & evidence

ORD record
ord-6fef3085a52e423b97bb333839e1fd2f
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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