Pyrrolidine → HCID 69946308, compound

HRID 635819Notes

Reaction equation

HRID 635819 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](=[O:21])[CH2:5][C:6]1[CH:10]=[C:9]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15](Cl)=[CH:14][CH:13]=2)[N:8]([CH3:20])[CH:7]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[ClH:1].[N:22]1([CH2:2][CH2:3][C:4](=[O:21])[CH2:5][C:6]2[CH:10]=[C:9]([C:11](=[O:19])[C:12]3[CH:17]=[CH:16][C:15]([N:8]4[CH2:9][CH2:10][CH2:6][CH2:7]4)=[CH:14][CH:13]=3)[N:8]([CH3:20])[CH:7]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 57060273HCID 57060273, compound

Product 1

HCID 69946308HCID 69946308, compoundYield 9%

Procedure

A 10 g (0.03 mole) sample of 4-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-butanone was added to 18 mL (0.216 mole) of pyrrolidine and the mixture heated under reflux for 4 h. The solvent was evaporated in vacuo and the residue triturated with Et2O. The mixture was filtered and the filtrate treated with ethereal HCl to give the salt. Recrystallization from CH3CN gave 1.18 g (9% yield) of a yellow solid: mp 203-206° C. 1H NMR (Me2SO-d6) d 1.85-2.05 (m, 10H); 2.87-3.05 (m, 4H); 3.1-3.15 (m, 2H); 3.3-3.4 (m, 4H); 3.45-3.55 (broad s, 2H); 3.9 (s, 3H); 6.62 (d, 2H); 6.96 (s,1H); 7.72 (d, 2H); 7.92 (s, 1H). Anal Calcd for C24H31N3O2-HCl-0.4CH3CN: C, 66.73; H, 7.50; N, 10.67. Found: C, 66.34; H, 7.43; N, 10,33.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 4 h
  3. customThe solvent was evaporated in vacuo
  4. customthe residue triturated with Et2O
  5. filtrationThe mixture was filtered
  6. additionthe filtrate treated with ethereal HCl
  7. customto give the salt
  8. customRecrystallization from CH3CN

Sources & evidence

ORD record
ord-ae1c486f105342029c38378da5e141f2
Source dataset
uspto-grants-2001_02
Patent number
US06191142B1

Reaction notes

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