Piperidine → HCID 21490881, compound

HRID 1973897Notes

Reaction equation

HRID 1973897 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:5](Cl)[N:4]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:5]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:4]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 21490887HCID 21490887, compound

Product 1

HCID 21490881HCID 21490881, compound

Procedure

46.8 g (0.2 mol) of 2-hydroxymethyl-4,6-dichloro-5-n-butyl-pyridine dissolved in 425 g (5 mols) of piperidine are heated for 20 hours at 190° in a bomb tube. The reaction mixture is then evaporated and the piperidine which still adheres is distilled off by means of toluene. The residue is rendered alkaline with 2 N sodium carbonate solution and the mixture is extracted with ether. The ether phases are combined, dried over sodium sulphate, filtered and evaporated. Fractional distillation of the residue in a high vacuum yields 2-hydroxymethyl-4-chloro-5-n-butyl-6-piperidino-pyridine of the formula ##STR17## and of boiling point 147°-152° (0.25 mm Hg).

Workup

  1. temperatureare heated for 20 hours at 190° in a bomb tube
  2. customThe reaction mixture is then evaporated
  3. distillationthe piperidine which still adheres is distilled off by means of toluene
  4. extractionthe mixture is extracted with ether
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. distillationFractional distillation of the residue in a high vacuum

Sources & evidence

ORD record
ord-8dec4c71afc64d7ba1dff8a8ffe43259
Source dataset
uspto-grants-1976_12
Patent number
US03998955

Reaction notes

Loading…