1,2,3,6-Tetrahydropyridine → HCID 178501988, compound

HRID 1285194Notes

Reaction equation

HRID 1285194 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[N+:5]([O-:13])=[C:4]([NH:14][C:15]([O:17][CH3:18])=[O:16])[CH:3]=1.[NH:19]1[CH2:24][CH2:23][CH:22]=[CH:21][CH2:20]1>C(Cl)Cl>[N:19]1([C:2]2[N:7]=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[N+:5]([O-:13])=[C:4]([NH:14][C:15]([O:17][CH3:18])=[O:16])[CH:3]=2)[CH2:20][CH:21]=[CH:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 127501,2,3,6-TetrahydropyridineHCID 178501976HCID 178501976, compound

Product 1

HCID 178501988HCID 178501988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 5.0 g (0.018 mol) of dimethyl 6-chloro-2,4-pyrimidinedicarbamate 3-oxide in 100 ml of methylene chloride is treated with 10 ml (0.22 mol) of 1,2,5,6-tetrahydropyridine and the mixture is heated to boiling for 3 hours under an argon atmosphere and while stirring. The mixture is evaporated under vacuum, the residue is taken up in chloroform, the organic phase is washed with water, dried over sodium sulphate and evaporated under vacuum. By recrystallization of the residue from methylene chloride/ethyl acetate there is obtained pure dimethyl 6-[3,6-dihydro-1(2H)-pyridyl]-2,4-pyrimidinedicarbamate 3-oxide in the form of white crystals of melting point 206°.

Workup

  1. temperaturethe mixture is heated
  2. customThe mixture is evaporated under vacuum
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated under vacuum
  6. customBy recrystallization of the residue from methylene chloride/ethyl acetate there

Sources & evidence

ORD record
ord-fff876223a9d49f6b3507e41156f5ed4
Source dataset
uspto-grants-1986_01
Patent number
US04565869

Reaction notes

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