Hydrochloric Acid → 1-(4-Trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanone

HRID 1029822Notes

Reaction equation

HRID 1029822 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.[CH2:15]=O.Cl.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.Cl>>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:12])[CH:10]([CH3:15])[CH2:11][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 136554p-TrifluoromethylpropiophenoneHCID 212848Pyrrolidine, hydrochloride (1:1)

Product 1

HCID 99477501-(4-Trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanoneYield 44.8%

Procedure

A mixture of 1-(4-trifluoromethylphenyl)-1-propanone (2.50 g), paraformaldehyde (1.10 g), pyrrolidine hydrochloride (1.60 g), and hydrochloric acid (0.1 ml) was refluxed for 16 hours. The mixture was evaporated in vacuo to give the residue. The residue was partitioned into water and ethyl acetate. The aqueous layer was neutralized with ammonia water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was evaporated in vaccuo to give 1-(4-trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanone (1.58 g; yield: 44.8%) as an oil. ##STR317## 7.70 (2H, d, J=8.0 Hz, aromatic H), 8.05 (2H, d, J=8.0 Hz, aromatic H).

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe mixture was evaporated in vacuo
  3. customto give the residue
  4. customThe residue was partitioned into water and ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vaccuo

Sources & evidence

ORD record
ord-8fbb5ec62a494ce3893b37138917f7bf
Source dataset
uspto-grants-1992_04
Patent number
US05103022

Reaction notes

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