Piperidine → HCID 13034527, compound

HRID 2059208Notes

Reaction equation

HRID 2059208 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[C:11]([CH2:13]C(O)=O)#[N:12].[NH:17]1CCC[CH2:19][CH2:18]1>N1C=CC=CC=1>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH:1]([CH2:13][C:11]#[N:12])[CH2:19][C:18]#[N:17])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 9740Cyanoacetic acidHCID 115693-Methoxybenzaldehyde

Product 1

HCID 13034527HCID 13034527, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution consisting of 25 g of m-anisaldehyde, 47 g of cyanoacetic acid and 3 ml of piperidine in 120 ml of pyridine is placed in a suitable reaction vessel and kept in a 110° oil-bath for 22 hours. Most of the solvent is removed under reduced pressure and the remaining oil is dissolved in about 400 ml of toluene. The solution is washed sequentially with equal volumes of water, 10% hydrochloric acid and saturated sodium bicarbonate. The washed solution is then concentrated under vacuum and the residue is distilled to give 20.7 g of 3-(3-methoxyphenyl)glutaronitrile, bp 146°-153° at 0.01 mm.

Workup

  1. customis placed in a suitable reaction vessel
  2. customkept in a 110°
  3. customfor 22 hours
  4. customMost of the solvent is removed under reduced pressure
  5. dissolutionthe remaining oil is dissolved in about 400 ml of toluene
  6. washThe solution is washed sequentially with equal volumes of water, 10% hydrochloric acid and saturated sodium bicarbonate
  7. concentrationThe washed solution is then concentrated under vacuum
  8. distillationthe residue is distilled

Sources & evidence

ORD record
ord-4ccb71b4ba5d43debbe6cd774985339d
Source dataset
uspto-grants-1982_03
Patent number
US04322421

Reaction notes

Loading…