Toluene → HCID 86651391, compound

HRID 588286

Reaction equation

HRID 588286 reaction equation
[CH:1]([N:3]1[CH2:7]CC[CH2:4]1)=O.C[O:9][S:10]([O:13]C)(=O)=[O:11].[NH:15]1[CH2:19]CC[CH2:16]1.[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:20]1([CH3:26])[CH:25]=[CH:24][C:23]([S:10]([O-:13])(=[O:11])=[O:9])=[CH:22][CH:21]=1.[CH3:1][N:3]([CH3:7])[CH:4]=[N+:15]([CH3:19])[CH3:16]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 31268PyrrolidineHCID 773721-Pyrrolidinecarboxaldehyde

Product 1

HCID 86651391HCID 86651391, compound

Conditions

Temperature
80 °C

Procedure

A mixture of N-formylpyrrolidine (100 g) and dimethylsulfate (126 g) are heated to 80° C. for 4 h. Then a mixture of pyrrolidine (71 g) and toluene (100 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is concentrated in vacuo and triturated with diethyl ester. The precipitate is collected by filtration and recrystallised using ethyl acetate to give 1-pyrrolidin-1-ylmethylene-pyrrolidinium methylsulfate (18, R6/R7=Pyrrolidinyl). 1H NMR (DMSO-d6), 8.28 (1H), 3.90-3.85 (4H), 3.68-3.62 (4H), 3.38 (3H), 1.99-1.90 (4H), 1.86-1.77 (4H).

Workup

  1. additionare added
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction mixture is cooled to room temperature
  4. customthe phases are separated
  5. concentrationThe lower layer is concentrated in vacuo
  6. customtriturated with diethyl ester
  7. filtrationThe precipitate is collected by filtration
  8. customrecrystallised

Sources & evidence

ORD record
ord-fe923a1a2fcc4d27af9b3cd3216f6d4c
Source dataset
uspto-grants-2016_01
Patent number
US09227934B2

Linked notes

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