1-Methylpiperazine → 1-Methylpiperazine hydrochloride

HRID 1702444Notes

Reaction equation

HRID 1702444 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=[CH:17][S:18][CH:19]=[C:6]12)=[O:4].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>O1CCOCC1>[ClH:1].[ClH:1].[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:2][C:3]([N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8](=[O:16])[C:7]3=[CH:17][S:18][CH:19]=[C:6]23)=[O:4])[CH2:23][CH2:22]1.[ClH:1].[CH3:8][N:9]1[CH2:7][CH2:6][NH:5][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 200638994-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 2

HCID 121968951-Methylpiperazine hydrochlorideHCID 205037629,10-dihydro-4-[(4-methylpiperazin-1-yl)acetyl]-4H-thieno[3,4-b][1,5]benzodiazepin-10-one dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

14.9 g of 4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one, 21 g of N-methylpiperazine and 70 ml of dioxane are stirred at 80° C. for 1 hour, and the obtained solution is concentrated to dryness in vacuo. 150 ml of isopropanol and 40 ml of water are added to the resulting residue, and 25 ml of concentrated hydrochloric acid are then added dropwise; the thus prepared mixture is cooled in an ice-bath, and 9,10-dihydro-4-[(4-methylpiperazin-1-yl)acetyl]-4H-thieno[3,4-b][1,5]benzodiazepin-10-one dihydrochloride is obtained as a mixture 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 extracted exhaustively by shaking it with chloroform, and the organic solution is dried and concentrated to dryness in vacuo. 16 g of 9,10-dihydro-4-[(4-methylpiperazin-1-yl)acetyl]-4H-thieno[3,4 -b][1,5]benzodiazepin-10-one, m. 177° to 178° C. (from acetone), are thus obtained.

Workup

  1. concentrationthe obtained solution is concentrated to dryness in vacuo
  2. addition150 ml of isopropanol and 40 ml of water are added to the resulting residue, and 25 ml of concentrated hydrochloric acid
  3. additionare then added dropwise
  4. temperaturethe thus prepared mixture is cooled in an ice-bath

Sources & evidence

ORD record
ord-2b3f782196ea417998830ecf4c7dc9a0
Source dataset
uspto-grants-1983_04
Patent number
US04381301

Reaction notes

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