Benzyl Bromide → HCID 131726961, compound

HRID 747677Notes

Reaction equation

HRID 747677 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[O:6][CH2:7][CH2:8][NH:9][C:10]([CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:28]([N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][C:10]([NH:9][CH2:8][CH2:7][O:6][C:5]2[CH:19]=[CH:20][CH:21]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:11])[CH2:18][CH2:17]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 131726959HCID 131726959, compound

Product 1

HCID 131726961HCID 131726961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

430 mg (1.58 mmol) of N-[2-(3-cyanophenoxy)ethyl]piperidine-4-carboxyamide was dissolved in 10 ml of dimethylformamide. 540 mg (3.93 mmol) of potassium carbonate and 0.16 ml (1.31 mmol) of benzyl bromide were added to the solution, and they were stirred at 50° C. for 13 hours. After the treatment with ethyl acetate as the extractant in an ordinary manner, crude 1-benzyl-N-[2-(3-cyanophenoxy)ethyl]piperidine-4-carboxyamide was obtained. The crude product was stirred in 10 ml of dioxane containing 4 N hydrogen chloride. 3.5 ml of ethanol containing 30% (w/v) of hydrogen chloride was added to the resultant mixture. After the stirring at room temperature for 3 days, the solvent was evaporated under reduced pressure. The residue was dissolved in 20 ml of 10% (w/v) solution of ammonia in ethanol, and the obtained solution was stirred at room temperature for 2 days. The solvent was evaporated, and the residue was treated by the reversed-phase high-performance liquid chromatography with silica gel, containing octadodecyl group chemically bonded thereto, as the filler. After the elution with a mixed solvent of water and acetonitrile containing 0.1% (v/v) of trifluoroacetic acid, the fraction of the intended product was freeze-dried to obtain the title compound.

Sources & evidence

ORD record
ord-5ff9e89bfa014d60adea4bc364e823cb
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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