Water → HCID 86755043, compound

HRID 849462Notes

Reaction equation

HRID 849462 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:22])[CH:12]([CH2:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:13][CH2:14][C:3]=12.O.[C@@:24]12([CH2:34][S:35]([OH:38])(=[O:37])=[O:36])[C:31]([CH3:33])([CH3:32])[CH:28]([CH2:29][CH2:30]1)[CH2:27][C:25]2=[O:26].O>C(O)C>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:22])[CH:12]([CH2:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:13][CH2:14][C:3]=12.[CH3:32][C:31]1([CH3:33])[C:24]2([CH2:34][S:35]([OH:38])(=[O:37])=[O:36])[C:25]([CH2:27][CH:28]1[CH2:29][CH2:30]2)=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 125368FK 1052HCID 86755044HCID 86755044, compound

Product 1

HCID 86755043HCID 86755043, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
35 °C

Procedure

(±)8,9-dihydro-10-methyl-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (100 g), (1R)-(-)-10-camphorsulfonic acid monohydrate (85.3 g), and radiolite (1 g) in ethanol (1,000 ml) were heated under reflux. It was cooled to 35° C., and 0.2 g of seed crystals were added thereto, thereafter it was agitated at an interior temperature of 20~30° C. for 3 hr, and after ethanol (1,000 ml) was added therto, it was agitated overnight at 20~30° C. The following day, water (25 ml) was added thereto and it was agitated for 1 hr at 20~30° C., and after the temperature was raised to 33~37° C., it was agitated for 30 min. It was cooled to 20~30° C., thereafter the precipitated crystals were collected by filtration, washed with ethanol (100 ml), and dried overnight under vacuum to obtain (+)8,9-dihydro-10-methyl-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one·CSA salt as colorless coarse crystals.

Workup

  1. temperatureunder reflux
  2. addition0.2 g of seed crystals were added
  3. stirringwas agitated overnight at 20~30° C
  4. stirringit was agitated for 1 hr at 20~30° C.
  5. temperatureafter the temperature was raised to 33~37° C.
  6. stirringit was agitated for 30 min
  7. temperatureIt was cooled to 20~30° C.
  8. filtrationthe precipitated crystals were collected by filtration
  9. washwashed with ethanol (100 ml)
  10. customdried overnight under vacuum

Sources & evidence

ORD record
ord-79c5dfb6925d4973955a50d434aaee2d
Source dataset
uspto-grants-2000_01
Patent number
US06013653

Reaction notes

Loading…