Acetone → HCID 67177037, compound

HRID 1966008Notes

Reaction equation

HRID 1966008 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[CH2:15]=O.O.[CH3:18][C:19]([CH3:21])=[O:20]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:15][CH2:18][C:19](=[O:20])[CH3:21])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 34467312-(3,4-dichlorophenyl)pyrrolidine

Product 1

HCID 67177037HCID 67177037, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To the solution of 4 g (18.5 mmol) 2-(3,4-dichlorophenyl)-pyrrolidine in 10 ml acetone, during ice-water cooling, the mixture of 10 ml acetone and 1.6 ml cc. hydrochloric acid is added. The mixture is stirred for 15 minutes under cooling for 10 minutes at room temperature, then the solution of 0.83 g (9.3 mmol) paraformaldehyde in 9.2 ml iso-propanol is added and the reaction mixture is heated at reflux temperature for 4 hours. After cooling, 15 ml of water is added and the mixture is extracted with 3×20 ml dichloromethane, dried over sodium sulfate and evaporated in vacuum. The residue is crystallized in hexane to obtain 2.11 g title compound. Mp: 160-162° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux temperature for 4 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with 3×20 ml dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuum
  7. customThe residue is crystallized in hexane

Sources & evidence

ORD record
ord-bf23fe56ee164ce295a328208b527835
Source dataset
uspto-grants-2013_04
Patent number
US08420636B2

Reaction notes

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