Pyridine → HCID 9801910, compound

HRID 380572Notes

Reaction equation

HRID 380572 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:14][NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:37])[C:29]1[C:30]([O:35][CH3:36])=[CH:31][CH:32]=[CH:33][CH:34]=1.CCOCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:14][NH:15][C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])=[O:37])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 889692-Methoxybenzoyl chlorideHCID 8042381-Benzyl-4-phenylpiperidine-4-methylamine

Product 1

HCID 9801910HCID 9801910, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.1 g (7.6 mmol) of 1-N-Benzyl-4-phenyl-4-aminomethylpiperidine and 1.2 mL of pyridine (15.2 mmol) and 20 mg of 4-dimethylaminopyridine (DMAP) in 20 mL of methylene chloride was added 2.6 g (15.2 mmol) of o-anisoyl chloride at 0° C. The reaction mixture was stirred for 12 hr and was poured into 200 ml of ether. It was washed with saturated NaHCO3 solution, dried over MgSO4 and concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 1:4) to afford the title compound.

Workup

  1. washIt was washed with saturated NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (silica, hexanes: ethyl acetate, 1:4)

Sources & evidence

ORD record
ord-6a00bd75ceaa4ad592af22f4a34b2aab
Source dataset
uspto-grants-2001_10
Patent number
US06303637B1

Reaction notes

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