Toluene → Ethyl 4-(2-pyrimidinylimino)-1-piperidinecarboxylate

HRID 1736346Notes

Reaction equation

HRID 1736346 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[N:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[NH2:19].CC1C=CC=CC=1>C(O)(=O)C.O>[N:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[N:19]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 79782-AminopyrimidineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 21460901Ethyl 4-(2-pyrimidinylimino)-1-piperidinecarboxylateYield 101.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of 34 g of ethyl 4-oxo-1-piperidinecarboxylate, 20 g of 2-pyrimidinamine, 8 drops of acetic acid and 103.5 ml of methylbenzene was stirred for 28 hours at reflux temperature using a water-separator. The reaction mixture was evaporated, yielding 50 g of ethyl 4-(2-pyrimidinylimino)-1-piperidinecarboxylate as a residue (interm. 18).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-103ba6a931214fb9bc5818708d73d134
Source dataset
uspto-grants-1996_07
Patent number
US05541180

Reaction notes

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