HCID 20538743, compound → HCID 13216230, compound

HRID 1065232Notes

Reaction equation

HRID 1065232 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[O:13])[CH:4]=1>O=[Pt]=O.C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]([NH:11][C:12]([CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[O:13])[CH:4]=1

Participants

4

Reactant 1

HCID 20538743HCID 20538743, compound

Product 1

HCID 13216230HCID 13216230, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

4-Chloro-2-(4-pyridinecarboxamido)anisole hydrochloride (from E14) (10 g) was hydrogenated over Adams' catalyst (0.25 g) at 300 psi in ethanol (250 ml) at 70° for 6 hours. The residue obtained after filtration and evaporation was taken up in a mixture of ethyl acetate and aqueous sodium carbonate, the organic layer was dried (Na2CO3) filtered and evaporated to give 4-chloro-2-(piperidine-4-carboxamido)anisole as a cream-coloured powder (7.4 g). (A portion was recrystallised from ethyl acetate to give white prisms, m.p. 124°-126°.)

Workup

  1. customThe residue obtained
  2. filtrationafter filtration and evaporation
  3. additionwas taken up in a mixture of ethyl acetate and aqueous sodium carbonate
  4. dry with materialthe organic layer was dried (Na2CO3)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4ae43c211bf54293979648e4dbfa919d
Source dataset
uspto-grants-1982_05
Patent number
US04329344

Reaction notes

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