HCID 86742164, compound → HCID 20139846, compound

HRID 1252512Notes

Reaction equation

HRID 1252512 reaction equation
[O:1]=[C:2]1[CH:7](C(OCC2C=CC=CC=2)=O)[CH2:6][C:5](=[O:18])[NH:4][CH:3]1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H][H]>[Pd].C(OCC)(=O)C>[C:20]1([CH2:19][CH:3]2[NH:4][C:5](=[O:18])[CH2:6][CH2:7][C:2]2=[O:1])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 86742164HCID 86742164, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20139846HCID 20139846, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of (±)-3,6-dioxo-2-(phenylmethyl)-4-piperidinecarboxylic acid, phenylmethyl ester, 1.59 g (0.0047 mole) and 0.2 g of 20% palladium on carbon in 200 ml of ethyl acetate was exposed to hydrogen gas for 15 minutes, the suspension was purged with nitrogen gas, filtered, and the solvent evaporated in vacuo and the residue chromatographed using 100 g of silica gel and eluting with 200 ml of dichloromethane-methanol (98:2) and 200 ml of dichloromethane-methanol (97:3) to give (±)-6-(phenylmethyl)-2,5-piperidinedione, 0.8 g; mp 140°-141°.

Workup

  1. customthe suspension was purged with nitrogen gas
  2. filtrationfiltered
  3. customthe solvent evaporated in vacuo
  4. customthe residue chromatographed
  5. washeluting with 200 ml of dichloromethane-methanol (98:2) and 200 ml of dichloromethane-methanol (97:3)

Sources & evidence

ORD record
ord-59724c8061584aac9a26e077b591a149
Source dataset
uspto-grants-1988_05
Patent number
US04743585

Reaction notes

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