1-Methylpiperazine → 1,3-Dimethyl-4-[(4-methyl-1-piperazinyl)acetyl]-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

HRID 1902486Notes

Reaction equation

HRID 1902486 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])[CH: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>[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])=[CH:18]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 202615044-Chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

Product 1

HCID 205154321,3-Dimethyl-4-[(4-methyl-1-piperazinyl)acetyl]-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-oneYield 70.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.75 g of 4-chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one and 1.15 g of N-methylpiperazine in 50 ml of dry dioxane is warmed at 50° C. for 5 hours with stirring. After the mixture has cooled, the precipitate formed is filtered off. The filtrate is concentrated, 50 ml of saturated sodium bicarbonate solution are added, and the thus-prepared mixture is extracted several times with ethyl acetate. The combined extracts are dried over sodium sulfate and concentrated. 1.5 g of the title compound of m.p. 205° to 207° C. (from ethyl acetate) are obtained. M.p. of the dihydrochloride: 212° C. (D., from water). M.p. of the hemifumarate: 173° C. (from ethanol).

Workup

  1. temperatureAfter the mixture has cooled
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. concentrationThe filtrate is concentrated
  5. addition50 ml of saturated sodium bicarbonate solution are added
  6. extractionthe thus-prepared mixture is extracted several times with ethyl acetate
  7. dry with materialThe combined extracts are dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-56d7370443e04dce822d4196f34dc852
Source dataset
uspto-grants-1982_12
Patent number
US04363816

Reaction notes

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