Pyridine → 1-Cyclohexyl-4-chloromethyl-3,3-diphenyl-2-pyrrolidinone

HRID 614278Notes

Reaction equation

HRID 614278 reaction equation
[CH:1]1([N:7]2[CH2:11][CH:10]([CH2:12]O)[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:29])=O.N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:29][CH2:12][CH:10]1[CH2:11][N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8](=[O:26])[C:9]1([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 128222881-Cyclohexyl-4-hydroxymethyl-3,3-diphenyl-2-pyrrolidinone

Product 1

HCID 128222931-Cyclohexyl-4-chloromethyl-3,3-diphenyl-2-pyrrolidinoneYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 60.0 g. (0.17 mole) of 1-cyclohexyl-4-hydroxymethyl-3,3-diphenyl-2-pyrrolidinone in 400 ml. of chloroform was added 48.0 g. (0.40 mole) of thionylchloride with stirring. To this solution was added dropwise with ice bath cooling 40 g. (0.52 mole) of dry pyridine and the solution was refluxed for two hours. After concentrating in vacuo the residue was dissolved in chloroform and washed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution. The chloroform solution was dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was recrystallized from isopropyl ether and after drying weighed 34.5 g. (55% yield) and melted at 124°-126° C.

Workup

  1. additionTo this solution was added dropwise with ice bath
  2. temperaturecooling 40 g
  3. concentrationAfter concentrating in vacuo the residue
  4. dissolutionwas dissolved in chloroform
  5. washwashed successively with dilute hydrochloric acid solution and dilute sodium hydroxide solution
  6. dry with materialThe chloroform solution was dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from isopropyl ether
  10. customafter drying

Sources & evidence

ORD record
ord-6281927765f1478cbbd585082ccbe186
Source dataset
uspto-grants-1979_03
Patent number
US04144245

Reaction notes

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