1-Methylpiperazine → HCID 86745733, compound

HRID 1031180Notes

Reaction equation

HRID 1031180 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[N:17]([CH3:18])[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5]1.C(O)(C)C.[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[CH3:18][N:17]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5][CH:4]1[CH2:3][CH2:2][N:37]1[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]1

Participants

4

Reactant 3

HCID 531671-MethylpiperazineHCID 198197592-(2-Chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-oneHCID 86745734Fumaric acid isopropyl alcohol

Product 1

HCID 86745733HCID 86745733, compound

Conditions

Temperature
60 °C

Procedure

To 20 mL of N-methylpiperazine was added 3.0 g (0.01 mol) of 2-(2-chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one. The reaction mixture was heated to 60° C. for 24 hr. The excess amine was removed at 70° C., 0.5 mm Hg. The residual oil was taken up in 60 mL of CH2Cl2 and washed with 2×50 mL of 1N NaOH. The organic layer was dried over Na2SO4, filtered, concentrated by rotary evaporation, and further concentrated at 90° C., 0.5 mm Hg. The residual oil/glass was treated with 2 equivalent of fumaric acid isopropyl alcohol to give 3.4 g of solid. This was recrystallized from isopropyl alcohol to give 3.0 g (51%) off-white analytically pure material, mp 171°-79° C.

Workup

  1. customThe excess amine was removed at 70° C.
  2. washwashed with 2×50 mL of 1N NaOH
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. concentrationfurther concentrated at 90° C.

Sources & evidence

ORD record
ord-8d2efe37b54f41a68976cb4e18bc5e84
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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