Acetonitrile → HCID 14987178, compound

HRID 2051516Notes

Reaction equation

HRID 2051516 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:13]([CH3:24])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>CN(C)C1C=CN=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([C:28](=[O:31])[CH2:29][CH3:30])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:13]([CH3:24])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 62324Propionyl chlorideHCID 14987150HCID 14987150, compound

Product 1

HCID 14987178HCID 14987178, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of trans-N-benzyloxycarbonyl-3-methyl-4-phenylaminopiperidine (1.5 g, 4.6 mmol), 4-dimethylaminopyridine (375 mg, 3.1 mmol), and acetonitrile (10 ml) is added propionyl chloride (3.6 ml, 41 mmol). The solution is stirred and refluxed for 30 minutes, cooled to room temperature, and diluted with a saturated solution of sodium carbonate (30 ml). The resultant mixture is extracted with ethyl acetate (2×30 ml) and the organic phases combined, dried over magnesium sulfate, and concentrated to an oily residue which is chromatographed on silica gel (1/1 EtOAc/Hex) to give trans-N-benzyloxycarbonyl-3-methyl-4-[(1-oxopropyl)-phenylamino]piperidine as an oil: 1.6 g, 91%.

Workup

  1. temperaturerefluxed for 30 minutes
  2. extractionThe resultant mixture is extracted with ethyl acetate (2×30 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to an oily residue which
  5. customis chromatographed on silica gel (1/1 EtOAc/Hex)

Sources & evidence

ORD record
ord-c87de40f669f4638b33a22dd93a51bf0
Source dataset
uspto-grants-1991_05
Patent number
US05019583

Reaction notes

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