HCID 135563250, compound → HCID 10313361, compound

HRID 1005331Notes

Reaction equation

HRID 1005331 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[N:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O-:14])=O>[Pt]=O.C(O)C>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1=[O:14]

Participants

4

Reactant 1

HCID 135563250HCID 135563250, compound

Product 1

HCID 10313361HCID 10313361, compoundYield 139.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 150 g of 5-[[(1H-pyrrol-2-yl)methylen]amino]pentanoate and 120 g of ethanol was hydrogenated at 3.105Pa and at ambient temperature with 3.3 g of platinum oxide. After the calculated amount of hydrogen was consumed, the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in dichloromethane and the organic phase was washed three times with a sodium hydroxide 3N solution. The product was distilled at 13.30 Pa (bp. 100-130° C. The residue was crystallized from cyclohexane and hexane. The product was filtered off and dried, yielding 193 g (100%) of 1-(1H-pyrrol-2-ylmethyl)-2-piperidone; mp. 105.8° C.

Workup

  1. customAfter the calculated amount of hydrogen was consumed
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthe organic phase was washed three times with a sodium hydroxide 3N solution
  6. distillationThe product was distilled at 13.30 Pa (bp. 100-130° C
  7. customThe residue was crystallized from cyclohexane and hexane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-8a640bd4ff59437a810085def6a14557
Source dataset
uspto-grants-2000_04
Patent number
US06054468

Reaction notes

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