Pyrrolidine → HCID 69946308, compound

HRID 841038Notes

Reaction equation

HRID 841038 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, 10 H); 2.87-3.05 (m, 4 H); 3.1-3.15 (m, 2 H); 3.3-3.4 (m, 4 H); 3.45-3.55 (broad s, 2 H); 3.9 (s, 3H); 6.62 (d, 2 H); 6.96 (s, 1 H); 7.72 (d, 2 H); 7.92 (s, 1 H). 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-6e478dbcd99c491f852d39102737496d
Source dataset
uspto-grants-2002_04
Patent number
US06369228B2

Reaction notes

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