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

HRID 345498

Reaction equation

HRID 345498 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 (2.50g), paraformaldehyde (1.10g), pyrrolidine hydrochloride (1.60g), 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-1propanone (1.58g; yield: 44.8%) as an oil.

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-6e92e8cdde03423680812f606fb4b53a
Source dataset
uspto-grants-1991_10
Patent number
US05057535

Linked notes

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