Hydrochloric Acid → ethyl (2E)-3-[6-(4-piperidylamino)-3-pyridyl]acrylate dihydrochloride

HRID 226332Notes

Reaction equation

HRID 226332 reaction equation
[CH2:1]([O:3][C:4](=[O:27])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[N:11][CH:12]=1)[CH3:2].[ClH:28]>CCO.O1CCOCC1>[ClH:28].[ClH:28].[NH:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:10]2[N:11]=[CH:12][C:7](/[CH:6]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:27])=[CH:8][CH:9]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68960290tert-butyl 4-({5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-2-pyridyl}amino)-1-piperidinecarboxylate

Product 1

HCID 86603643ethyl (2E)-3-[6-(4-piperidylamino)-3-pyridyl]acrylate dihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of tert-butyl 4-({5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-2-pyridyl}amino)-1-piperidinecarboxylate (2.8 g) in EtOH (20 ml) was added 4N HCl in dioxane (18.6 ml), the mixture was stirred at 23° C. for 30 minutes. The precipitate was collected, washed with IPE, dried under reduced pressure to give ethyl (2E)-3-[6-(4-piperidylamino)-3-pyridyl]acrylate dihydrochloride.

Workup

  1. customThe precipitate was collected
  2. washwashed with IPE
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-68e6077fe54d44ff84b0e8f53fe3baec
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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