Piperidine → HCID 178427998, compound

HRID 1764100Notes

Reaction equation

HRID 1764100 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7](Cl)[CH:6]=[C:5]([CH3:10])[N+:4]=1[O-:11].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>O>[NH2:2][C:3]1[CH:8]=[C:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:6]=[C:5]([CH3:10])[N+:4]=1[O-:11]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 178426121HCID 178426121, compound

Product 1

HCID 178427998HCID 178427998, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
155 °C

Procedure

A quantity (1.50 g., 0.0077 mole) of 2-amino-4-chloro-6-methylpyridine-1-oxide hydrochloride (prepared in Part B, above) with 6.0 ml. piperidine, and 10.0 ml. water was sealed in a reinforced bottle and heated in an oil bath at the temperature 155° C. for 3.5 hrs. The aqueous reaction mixture was then cooled to 25° C. and diluted with 50 ml. water. The diluted reaction mixture was then extracted with three 50.0 ml. portions of chloroform. The combined chloroform extracts were treated with charcoal, dried over anhydrous sodium sulfate, filtered, and the chloroform was removed by evaporation under reduced pressure. The solid residue thus obtained was crystallized from acetone to give 0.88 g. (55% yield) of 2-amino-6-methyl-4-piperidinopyridine-1-oxide as off-white needles having a melting point at 260° C. (with decomposition). The crystals sinter at about 250° C.

Workup

  1. temperatureThe aqueous reaction mixture was then cooled to 25° C.
  2. additiondiluted with 50 ml
  3. customThe diluted reaction mixture
  4. extractionwas then extracted with three 50.0 ml
  5. additionThe combined chloroform extracts were treated with charcoal
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe chloroform was removed by evaporation under reduced pressure
  9. customThe solid residue thus obtained
  10. customwas crystallized from acetone
  11. customto give 0.88 g

Sources & evidence

ORD record
ord-58e8eec78b4942d2aef09a05023026b4
Source dataset
uspto-grants-1978_09
Patent number
US04115396

Reaction notes

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