Potassium Hydroxide → N-(Piperidin-4-yl)pyridin-2-amine

HRID 26738Notes

Reaction equation

HRID 26738 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH:8]1[CH2:13][CH2:12][N:11](C(OCC)=O)[CH2:10][CH2:9]1.[OH-].[K+]>CC(O)C>[NH:11]1[CH2:12][CH2:13][CH:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11357119Ethyl 4-(pyridin-2-ylamino)piperidine-1-carboxylate

Product 1

HCID 21912674N-(Piperidin-4-yl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 90 parts of ethyl 4-(2-pyridinylamino)-1-piperidinecarboxylate, 90 parts of potassium hydroxide and 720 parts of 2-propanol is stirred and refluxed for 2 days. The reaction mixture is evaporated. 1000 Parts of water are added to the residue and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane, yielding 13 parts of N-(4-piperidinyl)-2-pyridinamine.

Workup

  1. temperaturerefluxed for 2 days
  2. customThe reaction mixture is evaporated
  3. addition1000 Parts of water are added to the residue
  4. extractionthe product is extracted with dichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-01e4b8e38dab42e49a6afd56c1ffd7a7
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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