1-Methylpiperazine → HCID 20549839, compound

HRID 2058598Notes

Reaction equation

HRID 2058598 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[C:7]2[N:17]([CH3:21])[N:18]=[C:19]([CH3:20])[C:6]1=2)=[O:4].[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>O1CCOCC1>[ClH:1].[ClH:1].[CH3:21][N:17]1[C:7]2[C:8](=[O:16])[NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]([C:3](=[O:4])[CH2:2][N:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)[C:6]=2[C:19]([CH3:20])=[N:18]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 205498784-Chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one

Product 1

HCID 20549839HCID 20549839, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

15.0 g of 4-chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one, 21 g of N-methylpiperazine and 70 ml of dioxane are stirred at 80° C. for 1 hour (complete reaction being already indicated by a thin layer chromatogram after 20 minutes), and the thus-obtained solution is concentrated to dryness in vacuo. 150 ml of isopropanol and 40 ml of water are added to the residue, 25 ml of concentrated hydrochloric acid are then added dropwise and the resulting mixture is cooled in an icebath to obtain 1,3-dimethyl-4-[(4-methylpiperazin-1-yl)acetyl]-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one dihydrochloride mixed with N-methylpiperazine hydrochloride. The hydrochlorides are dissolved in water and chloroform, the pH is adjusted to 8.2 with 2 N sodium hydroxide solution, the aqueous phase is exhaustively extracted by shaking it with chloroform and the organic solution is dried and concentrated to dryness in vacuo. This yields 17.6 g of 1,3-dimethyl-4-[(4-methylpiperazin-1-yl)acetyl]-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one, mp 186° to 188° C. (from toluene); dihydrochloride, mp 222° to 224° C. (dec.); hemi fumarate, mp 257° to 258° C. (dec.).

Workup

  1. customcomplete reaction
  2. concentration), and the thus-obtained solution is concentrated to dryness in vacuo
  3. addition150 ml of isopropanol and 40 ml of water are added to the residue, 25 ml of concentrated hydrochloric acid
  4. additionare then added dropwise
  5. temperaturethe resulting mixture is cooled in an icebath

Sources & evidence

ORD record
ord-ef2b29816ac348b7acd4dcc0d043a9aa
Source dataset
uspto-grants-1982_03
Patent number
US04317823

Reaction notes

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