Dichloromethane → HCID 54886864, compound

HRID 244995Notes

Reaction equation

HRID 244995 reaction equation
[C-:1]#[N:2].[Na+].[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.ClCCl>C(O)(=O)C.CC(C)=O>[CH3:12][N:13]1[CH2:18][CH2:17][C:16]([NH:4][C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)([C:1]#[N:2])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7813p-ToluidineHCID 8929Sodium CyanideHCID 740491-Methyl-4-piperidone

Product 1

HCID 54886864HCID 54886864, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

Sodium cyanide (0.318 g, 6.5 mmol) was added to a mixture of p-toluidine (0.535 g, 5 mmol) and 1-methyl-4-piperidinone (0.678 g, 6 mmol) in acetic acid 90% (5 ml). The reaction mixture was stirred at room temperature for 6 h and then 100 ml of dichloromethane was added. The organic layer was washed with a solution NaOH, 2N (2×50 ml), dried over magnesium sulfate, concentrated and chromatographed (DCM and then acetone) to obtained 27a (0.722 g, 3.15 mmol, 63%).

Workup

  1. washThe organic layer was washed with a solution NaOH, 2N (2×50 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customchromatographed (DCM

Sources & evidence

ORD record
ord-a571f47eccd04df9ae35bd46b3804f00
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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