1-Methylpiperazine → Zolenzepine

HRID 2058597Notes

Reaction equation

HRID 2058597 reaction equation
Cl[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.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=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

5

Reactant 3

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 205498784-Chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one

Product 1

HCID 3086085ZolenzepineYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.5 g of 4-chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one, 8.1 g of N-methylpiperazine and 50 ml of toluene are stirred at 80° C. for 2 hours. 60 ml of dilute sodium bicarbonate solution are added to the mixture, the layers are separated and the aqueous phase is extracted by shaking it with toluene several times more before concentrating it to dryness in vacuo. The residue is stirred with 100 ml of isopropanol and is filtered; the filtrate is concentrated in vacuo. The residue (4.0 g) is purified by stirring it with diethyl ether and by recrystallizing it from toluene, which yields 2.2 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.; succinate, mp 172° to 174° C.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous phase is extracted
  3. concentrationbefore concentrating it to dryness in vacuo
  4. stirringThe residue is stirred with 100 ml of isopropanol
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue (4.0 g) is purified
  8. stirringby stirring it with diethyl ether
  9. customby recrystallizing it from toluene, which

Sources & evidence

ORD record
ord-b7eea1709e14428d857ae28f11abc5f5
Source dataset
uspto-grants-1982_03
Patent number
US04317823

Reaction notes

Loading…