Pyrrolidin-1-amine monohydrochloride → HCID 14578742, compound

HRID 704744Notes

Reaction equation

HRID 704744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][C:18](=O)[CH:19]([CH3:21])[CH3:20])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:18]([CH:19]([CH3:21])[CH3:20])[N:24]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 143002712-(4-Fluorophenyl)-5-methyl-1-phenylhexane-1,4-dione

Product 1

HCID 14578742HCID 14578742, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g of molecular sieve 3 Å are added to 15 g (50 mmol) of the compound from Example 2 and 20 g (164 mmol) of N-aminopyrrolidine hydrochloride in 150 ml of toluene AR and the mixture is heated to reflux for 48 hours. The mixture is cooled, filtered and washed well with toluene. The toluene solutions are combined and extracted 3×using 1N hydrochloric acid. The organic phase is subsequently washed using saturated sodium hydrogen carbonate solution, dried over magnesium sulphate and concentrated in vacuo. The residue is stirred with a little ethanol, cooled and filtered off with suction. After drying in a desiccator, 2.3 g of substance are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 48 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washwashed well with toluene
  6. extractionextracted 3×
  7. washThe organic phase is subsequently washed
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated in vacuo
  10. temperaturecooled
  11. filtrationfiltered off with suction
  12. customAfter drying in a desiccator
  13. custom2.3 g of substance are obtained

Sources & evidence

ORD record
ord-fc405942416745cd910ff6c2d1936186
Source dataset
uspto-grants-1991_01
Patent number
US04988711

Reaction notes

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