Allyl bromide → HCID 10319122, compound

HRID 2103734Notes

Reaction equation

HRID 2103734 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[CH:35]=[CH2:36]>C(#N)C.O>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4](=[O:25])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:36][CH:35]=[CH2:34])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1)[CH3:27]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 10406550HCID 10406550, compound2×

Product 1

HCID 10319122HCID 10319122, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N,N-diethyl-4-[benzyl(piperidin-4-yl)amino]benzamide (Compound 8) (0.25 g, 0.684 mmole) in 10 mL of acetonitrile was added potassium carbonate (0.10 g, 0.752 mmole) and allyl bromide (0.08 g, 0.684 mmol). The reaction mixture was stirred for six days under Argon and then was diluted with water (50 mL). This solution was extracted three times with dichloromethane (50 mL). The organic extracts were combined, washed with sodium carbonate solution, dried (Na2SO4), and concentrated to provide a yellow foam. This material was purified on a flash silica gel column (5% methanol-chloroform to 10% methanol-chloroform) to provide 0.11 g (40%) of N,N-diethyl-4-[benzyl(1-allylpiperidin-4-yl)amino]benzamide as a colorless oil. MS (ES), m/z 406 (MH+). 300 MHz 1H NMR (CDCl3) δ1.17 (t, J=7.0 Hz, 6H), 1.68-1.90 (m, 4H), 2.06 (br t, J=10.6 Hz, 2H), 2.91-3.08 (m, 4H), 3.31-3.52 (m, 4H), 3.75-3.92 (br m, 1H), 4.52 (s, 2H), 5.09-5.25 (m, 2H), 5.75-5.95 (m, 1H), 6.65 (d, J=8.7 Hz, 2H), 7.15-7.38 (m, 7H).

Workup

  1. extractionThis solution was extracted three times with dichloromethane (50 mL)
  2. washwashed with sodium carbonate solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto provide a yellow foam
  6. customThis material was purified on a flash silica gel column (5% methanol-chloroform to 10% methanol-chloroform)

Sources & evidence

ORD record
ord-02398d8c3d644488bbff11ecd28fc1b2
Source dataset
uspto-grants-2009_08
Patent number
US07576105B2

Reaction notes

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