4-Methylpiperidine → HCID 19823615, compound

HRID 728255Notes

Reaction equation

HRID 728255 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([CH:20](O)[C:21]#[N:22])[CH2:19][CH2:18][CH2:17]2)[CH:12]=[CH:13][C:14]=1[Cl:15]>C1(C)C=CC=CC=1.O.CCOCC>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([CH:20]([N:5]3[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]3)[C:21]#[N:22])[CH2:19][CH2:18][CH2:17]2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

6

Reactant 2

HCID 693814-MethylpiperidineHCID 19823670HCID 19823670, compound

Product 1

HCID 19823615HCID 19823615, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Methylpiperidine (4.8 g) was added to a solution of 2-[1-(3,4-dichlorophenyl)cyclobutyl]-2-hydroxyacetonitrile (12 g) in toluene (50 ml). The reaction mixture was stirred and heated at 100°-105° C. for two hours, cooled and diluted with water (100 ml) and ether (60 ml). The organic layer was separated washed with water and dried. Evaporation of the solvents gave an oil which solidified on standing to give a solid which was triturated with petroleum ether (b.p. 60°-80° C.) to give 2-[1-(3,4-dichlorophenyl)cyclobutyl]-2-(4-methylpiperidino)acetonitrile (m.p. 76°-78° C.).

Workup

  1. temperatureheated at 100°-105° C. for two hours
  2. temperaturecooled
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customEvaporation of the solvents
  7. customgave an oil which
  8. customto give a solid which
  9. customwas triturated with petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-58b3cdf07e9746a89eecd97c18b7b3b0
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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