Ethyl 4-(pyridin-2-ylamino)piperidine-1-carboxylate → N-(Piperidin-4-yl)pyridin-2-amine

HRID 1245449Notes

Reaction equation

HRID 1245449 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>Br>[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

3

Reactant 1

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

Product 1

HCID 21912674N-(Piperidin-4-yl)pyridin-2-amineYield 166.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6 g of ethyl 4-(pyridin-2-ylamino)piperidine-1-carboxylate (23a) were refluxed in 30 ml of 47% HBr for 6 h. Evaporation of the mixture, trituration of the resulting crude product with ethyl acetate/CH3OH (9:1) and renewed drying afforded 7.1 g of white solid; ESI-MS [M+H+]=178.15.

Workup

  1. customEvaporation of the mixture, trituration of the resulting crude product with ethyl acetate/CH3OH (9:1)
  2. customrenewed drying

Sources & evidence

ORD record
ord-a7ad09585266425da852695aa3693fbe
Source dataset
uspto-grants-2006_10
Patent number
US07125883B1

Reaction notes

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