1-Methylpiperazine → HCID 21422095, compound

HRID 259649Notes

Reaction equation

HRID 259649 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[CH:11]=[CH:10][C:9]=1[N:18]1[CH:26]([O:27][C:28](OC2C=CC=CC=2)=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:37].C(=O)(O)[O-].[Na+]>C(#N)C.C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:28]([O:27][CH:26]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:37])[N:18]2[C:9]2[CH:10]=[CH:11][C:12]3[C:17](=[N:16][CH:15]=[CH:14][CH:13]=3)[N:8]=2)=[O:29])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 21422079HCID 21422079, compound

Product 1

HCID 21422095HCID 21422095, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

4-Methylpiperazine (8 g.) is added all at once to a suspension of 2-(1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one (5.6 g.) in acetonitrile (100 cc.). The solution obtained is stirred for 6 hours at a temperature of about 20° C. The reaction mixture is poured into a suspension of ice (100 g.) in methylene chloride (300 cc.). An 8% aqueous solution of sodium bicarbonate (200 cc.) is added to the suspension obtained. The organic phase is decanted and the aqueous phase is extracted with methylene chloride (400 cc.). The combined organic phases are dried over anhydrous potassium carbonate (10 g.) and concentrated to dryness. The oily residue (8 g.) is taken up in refluxing diisopropyl ether (100 cc.). On cooling the solution, crystals are deposited and are filtered off. 3-(4-Methylpiperazin-1-yl)carbonyloxy-2-(1,8-naphthyridin-2-yl)isoindolin-1-one (2.9 g.), which melts at 183° C., is thus obtained.

Workup

  1. customThe solution obtained
  2. customobtained
  3. customThe organic phase is decanted
  4. extractionthe aqueous phase is extracted with methylene chloride (400 cc.)
  5. dry with materialThe combined organic phases are dried over anhydrous potassium carbonate (10 g.)
  6. concentrationconcentrated to dryness
  7. temperaturein refluxing diisopropyl ether (100 cc.)
  8. temperatureOn cooling the solution, crystals
  9. filtrationare filtered off

Sources & evidence

ORD record
ord-07416800b48147a7983187bb2b06ff87
Source dataset
uspto-grants-1977_07
Patent number
US04038391

Reaction notes

Loading…