Pyridine → HCID 12953546, compound

HRID 614276Notes

Reaction equation

HRID 614276 reaction equation
[C:1]1([C:7]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]([CH2:12]O)[CH2:10][N:9]([CH:14]([CH3:16])[CH3:15])[C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:26])=O.N1C=CC=CC=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:26][CH2:12][CH:11]1[CH2:10][N:9]([CH:14]([CH3:16])[CH3:15])[C:8](=[O:17])[C:7]1([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 12953545HCID 12953545, compound

Product 1

HCID 12953546HCID 12953546, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 43 g. (0.14 mole) of 3,3-diphenyl-4-hydroxymethyl-1-isopropyl-2-pyrrolidinone in 250 ml. of chloroform was treated with 33 g. (0.28 mole) of thionyl chloride over a one minute period followed by the dropwise addition of 22 g. (0.23 mole) of pyridine over a 30 minute period. The mixture was refluxed 18 hours and then poured onto ice. The cold mixture was made basic by the addition of sodium hydroxide. The chloroform layer was separated, dried over sodium sulfate and concentrated. The residue was crystallized using charcoal from a 25% ethyl acetate -- 75% isopropyl ether mixture. The crystalline solid was recrystallized from a 75% ethanol -- 25% water mixture and then from isopropyl ether. The dried 4-chloromethyl-3,3-diphenyl-1-isopropyl-2-pyrrolidinone weighed 23 g. and melted at 114°-116° C.

Workup

  1. temperatureThe mixture was refluxed 18 hours
  2. additionpoured onto ice
  3. customThe chloroform layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized
  7. customThe crystalline solid was recrystallized from a 75% ethanol

Sources & evidence

ORD record
ord-3f68320d4bc044fbbfe270754ad073fa
Source dataset
uspto-grants-1979_03
Patent number
US04144245

Reaction notes

Loading…