Piperidine → HCID 178507851, compound

HRID 848817Notes

Reaction equation

HRID 848817 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8]C(OCC)=O)[N+:5]([O-:14])=[C:4]([NH:15]C(OCC)=O)[CH:3]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[NH2:15][C:4]1[CH:3]=[C:2]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:7]=[C:6]([NH2:8])[N+:5]=1[O-:14]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 178473436HCID 178473436, compound

Product 1

HCID 178507851HCID 178507851, compoundYield 8%

Procedure

A mixture of 4-chloro-2,6-bis-(ethoxycarbonylamino)pyridine 1-oxide (10.0 g., 0.03 mole) obtained according to the procedure of Example 1(a) and 60 ml. of piperidine is heated in a sealed tube at 135° C. for a period of 48 hr. The reaction mixture is concentrated to dryness and the residual material taken up in a mixture of chloroform and 10% aqueous sodium carbonate. After separating the organic and aqueous fractions, the aqueous layer is washed with chloroform, the chloroform fractions combined and dried over magnesium sulfate. The dried chloroform extract is concentrated to a volume of approximately 100 ml., cooled and filtered to afford 0.52 g., (8% yield) of 2,6-diamino-4-(1-piperidinyl)pyridine 1-oxide, m.p. 249°-265° C. (dec.).

Workup

  1. customobtained
  2. concentrationThe reaction mixture is concentrated to dryness
  3. additionthe residual material taken up in a mixture of chloroform and 10% aqueous sodium carbonate
  4. customAfter separating the organic and aqueous fractions
  5. washthe aqueous layer is washed with chloroform
  6. dry with materialdried over magnesium sulfate
  7. extractionThe dried chloroform extract
  8. concentrationis concentrated to a volume of approximately 100 ml
  9. temperature, cooled
  10. filtrationfiltered
  11. customto afford 0.52 g

Sources & evidence

ORD record
ord-2aa8093cc875490ab7312a76b0b819b0
Source dataset
uspto-grants-1981_10
Patent number
US04297498

Reaction notes

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