1-Methylpiperazine → HCID 21444375, compound

HRID 328270Notes

Reaction equation

HRID 328270 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22]([O:24]C4C=CC=CC=4)=O)[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:31])=[N:9]2)=[CH:4][CH:3]=1.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>C(#N)C>[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22]([N:36]4[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]4)=[O:24])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:31])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 21422077HCID 21422077, compound

Product 1

HCID 21444375HCID 21444375, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

Following the procedure of Example 11 but starting with 2-(7-methyl-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one (4.9 g.) and 4-methylpiperazine (6 g.) in acetonitrile (40 cc.) and stirring the reaction mixture for 24 hours at 25° C., a crude product (4.2 g.) is obtained. This product is triturated in diethyl ether (42 cc.) and then recrystallised from diisopropyl ether (300 cc.). 2-(7-Methyl-1,8-naphthyridin-2-yl)-3-(4-methylpiperazin-1-yl)carbonyloxy-isoindolin-1-one (1.1 g.), melting at 190° C., is thus obtained.

Workup

  1. customa crude product (4.2 g.) is obtained
  2. customThis product is triturated in diethyl ether (42 cc.)
  3. customrecrystallised from diisopropyl ether (300 cc.)

Sources & evidence

ORD record
ord-727c95b3d8db4738b6f00584315fe16b
Source dataset
uspto-grants-1977_04
Patent number
US04016274

Reaction notes

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