1-Methyl-4-piperidone → HCID 54060679, compound

HRID 1608992Notes

Reaction equation

HRID 1608992 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[O:9]=[C:10]1[NH:14][C@@H:13]([CH2:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][CH:20]=[CH:19]3)[CH2:12][O:11]1>C(O)(=O)C>[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:19]2[C:18]3[C:22](=[CH:23][CH:24]=[C:16]([CH2:15][C@H:13]4[CH2:12][O:11][C:10](=[O:9])[NH:14]4)[CH:17]=3)[NH:21][CH:20]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 740491-Methyl-4-piperidoneHCID 53919388HCID 53919388, compound

Product 1

HCID 54060679HCID 54060679, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Methyl-4-piperidone (0.47 g, Aldrich) was added to a stirred solution of the product from step (b) (0.30 g) in glac. acetic acid (2.0 ml) and the mixture stirred at 100° C. for 2 hours. The cooled mixture was poured onto ice/NH4OH (20 ml) and the resulting solid filtered off. The latter was eluted through a silica column using DCM/EtOH/NH4OH (60:8:1) as eluant and crystallised from ethyl acetate to give the desired product as a colourless solid (0.11 g), mp 225°-227° C., [α]D20 -45.4° (c=0.5. 1N aqu. HCl). Elemental analysis and 1H NMR were consistent with the proposed structure.

Workup

  1. additionThe cooled mixture was poured onto ice/NH4OH (20 ml)
  2. filtrationthe resulting solid filtered off
  3. washThe latter was eluted through a silica column
  4. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-3663ab83e7084b05912400033c2d4396
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

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