Methanol → HCID 20482634, compound

HRID 2064201Notes

Reaction equation

HRID 2064201 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10](C(OCC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:22]=[C:23]([NH2:29])[C:24]([NH2:28])=[CH:25][C:26]=1[CH3:27].[C:30](OCC)(=[O:32])C.CO>C1(C)C(C)=CC=CC=1>[CH3:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]2[N:28]([C:11]3[CH2:12][CH2:13][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9][CH:10]=3)[C:30](=[O:32])[NH:29][C:23]=2[CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 102624Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate

Product 1

HCID 20482634HCID 20482634, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 1-benzyl-3-carbethoxy-4-piperidone (3 mmol, 784 mg) in xylene (20 mL) was treated at room temperature with 4,5-dimethyl-1,2-benzenediamine (3 mmol, 408.6 mg, 1 eq) and the suspension was stirred under reflux under argon overnight then further for 5 h. The mixture was concentrated under reduced pressure to give a brown residue, which was treated with ethyl acetate and a touch of methanol. Beige crystals formed from the brown solution and were filtered off and dried under reduced pressure (vacuum oven) to give the title compound (1.05 mmol, 350 mg, 35% yield). M+H 334.3.

Workup

  1. temperatureunder reflux under argon overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a brown residue, which
  4. customBeige crystals formed from the brown solution
  5. filtrationwere filtered off
  6. customdried under reduced pressure (vacuum oven)

Sources & evidence

ORD record
ord-862a1be8f11b49e9a23092d0ee595196
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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