Benzyl Bromide → N-[4-(1-Benzylpiperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide

HRID 1280761Notes

Reaction equation

HRID 1280761 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:23])[CH:15]=[CH:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC(C)=O>[CH2:30]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:23])[CH:15]=[CH:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:5][CH2:4]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69451641N-[4-(piperidine-4-yl)butyl]-3-(pyridin-3-yl)-acrylamide Dihydrochloride

Product 1

HCID 54513378N-[4-(1-Benzylpiperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

6.5 g (180 mmol) N-[4-(piperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide dihydrochloride (substance 22) are suspended in 80 ml acetone added to 9.9 g (72.0 mmol) potassium carbonate. A solution of 3.4 g (19.8 mmol) benzyl bromide in 10 ml acetone is added dropwise to this mixture at RT and stirred overnight. Subsequently, the suspension is filtered and the filtrate is concentrated under vacuum. The residue is taken up in 100 ml CHCl3 and washed with 30 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 (95/5 to 90/10) and crystallized from 15 ml acetonitrile after drawing off the solvent. Beige colored crystals with a MP of 88-90° C. were recovered; yield: 1.1 g (16%).

Workup

  1. filtrationSubsequently, the suspension is filtered
  2. concentrationthe filtrate is concentrated under vacuum
  3. washwashed with 30 ml water
  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 (95/5 to 90/10)
  7. customcrystallized from 15 ml acetonitrile
  8. customBeige colored crystals with a MP of 88-90° C. were recovered

Sources & evidence

ORD record
ord-a1b9fcf2a2fe49ce82d4f32830fda73f
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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