Water → 4-Piperidino-2,6-lutidine-1-oxide

HRID 1112463Notes

Reaction equation

HRID 1112463 reaction equation
Cl.Cl[C:3]1[CH:4]=[C:5]([CH3:11])[N+:6]([O-:10])=[C:7]([CH3:9])[CH:8]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.O>C(Cl)(Cl)Cl>[N:12]1([C:3]2[CH:4]=[C:5]([CH3:11])[N+:6]([O-:10])=[C:7]([CH3:9])[CH:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962Water2×HCID 8082PiperidineHCID 227642674-Chloro-2,6-lutidine-1-oxide hydrochloride

Product 1

HCID 227642734-Piperidino-2,6-lutidine-1-oxideYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A quantity (1.94 g., 0.01 mole) of 4-chloro-2,6-lutidine-1-oxide hydrochloride with 6 ml. piperidine, and 10 ml. water were sealed in a reinforced bottle and heated, with stirring, in an oil bath at the temperature 155° to 160° C. for 41/2 hrs. After cooling the reaction mixture to 25° C. and diluting it with 25 ml. water, several portions of chloroform were used to extract the objective product. The chloroform extracts were combined, dried over anhydrous sodium sulfate, treated with charcoal, and filtered. the filtrate was pale yellow. The chloroform was removed by evaporation under reduced pressure. The solid residue thus obtained was triturated with technical hexane (Skellysolve B, a mixture of isomeric hexanes having a boiling range between 142° and 156° F.) and then crystallized from about 10 ml. ethyl acetate. There was thus obtained 1.06 g. (50% yield) of 4-piperidino-2,6-lutidine-1-oxide as buff-colored crystals having a melting point at 87° to 90° C.

Workup

  1. temperatureheated
  2. additiondiluting it with 25 ml
  3. extractionto extract the objective product
  4. dry with materialdried over anhydrous sodium sulfate
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customThe chloroform was removed by evaporation under reduced pressure
  8. customThe solid residue thus obtained
  9. customwas triturated with technical hexane (Skellysolve B
  10. additiona mixture of isomeric hexanes having a boiling range between 142° and 156° F.) and
  11. customthen crystallized from about 10 ml

Sources & evidence

ORD record
ord-d1e13a5caac848fc8234ffab8f698a2e
Source dataset
uspto-grants-1978_10
Patent number
US04122264

Reaction notes

Loading…