Acetonitrile → HCID 86680282, compound

HRID 2202575Notes

Reaction equation

HRID 2202575 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:22][C:23]1[O:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(OCC)(=O)C.O>[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:22][C:23]2[O:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:24]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 75065Methyl 5-(chloromethyl)-2-furoateHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 86680282HCID 86680282, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 401 mg of 4-benzhydryloxypiperidine synthesized in Production Example 1, 288 mg of methyl 5-chloromethylfuran-2-carboxylate, 352 mg of potassium carbonate, and 3.5 mL of acetonitrile was stirred for 18 hours. The reaction solution was diluted with ethyl acetate and then thrown into water, and the organic layer was collected by separation. The organic layer was washed with a saturated saline solution and then dried over magnesium sulfate. The solvent was distilled off. The resulting product was subjected to a silica gel column chromatography (chloroform/acetone (volume ratio)=20:1 to 10:1) to give the title compound (475 mg).

Workup

  1. customthe organic layer was collected by separation
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-fa3b071a7bfb4eae99a30b89f56b7c77
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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