Pyrrolidine → HCID 23139177, compound

HRID 1171705Notes

Reaction equation

HRID 1171705 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCC1.[CH2:32]([O:34][C:35](=[O:44])[CH2:36][N:37]1[C:41]([CH:42]=O)=[CH:40][N:39]=[CH:38]1)[CH3:33]>C1C=CC=CC=1>[CH2:32]([O:34][C:35]([CH2:36][N:37]1[C:41](/[CH:42]=[C:10]2\[CH2:9][N:8]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:13][CH2:12][C:11]\2=[O:14])=[CH:40][N:39]=[CH:38]1)=[O:44])[CH3:33]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 27484141-Tritylpiperidin-4-oneHCID 71375228Ethyl (5-formyl-1H-imidazol-1-yl)acetate

Product 1

HCID 23139177HCID 23139177, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 1-(triphenylmethyl)piperidin-4-one (3.66 g) in benzene (40 ml) was added pyrrolidine (0.97 ml), and the mixture was heated under reflux for 3.5 hours. To this mixture was added a solution of ethyl(5-formyl-1H-imidazol-1-yl)acetate (1.95 g) in benzene (10 ml) under cooling using an ice bath. Then, the whole was heated further under reflux for 8.5 hours. After cooling, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure and the residue was purified by silica gel chromatography using hexane and ethyl acetate (1:3) as an eluent to afford the title compound (1.0 g, yield: 19%) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureunder cooling
  4. temperatureThen, the whole was heated further
  5. temperatureunder reflux for 8.5 hours
  6. temperatureAfter cooling
  7. customthe mixture was partitioned between water and ethyl acetate
  8. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationThe extract was concentrated under reduced pressure
  11. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4cbfddb593994c618c6c0c9de27c5ddc
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…