1-Methylpiperazine → 5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1-[2-(4-methyl-1-piperazinyl)ethyl]-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 441258Notes

Reaction equation

HRID 441258 reaction equation
[CH:1]([CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15](=[O:38])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:37])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)=[CH:18][CH:17]=2)[CH2:7][CH2:6][C:5]1=[O:39])=O.[CH3:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:36][C:33]1[CH:32]=[CH:31][C:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([C:15]([N:8]3[C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:4]([CH2:3][CH2:1][N:44]4[CH2:45][CH2:46][N:41]([CH3:40])[CH2:42][CH2:43]4)[C:5](=[O:39])[CH2:6][CH2:7]3)=[O:38])=[CH:17][CH:18]=2)=[O:37])=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 224052661-formylmethyl-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

Product 1

HCID 224050915-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1-[2-(4-methyl-1-piperazinyl)ethyl]-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-oneYield 26.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 1-formylmethyl-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (380 mg) and 4-methylpiperazine (73.4 mg) in a mixture of methanol (10 ml) and acetic acid (0.5 ml) was added sodium cyanoborohydride (46.1 mg) and the mixture was stirred at ambient temperature for 5 hours. The mixture was poured into a mixture of chloroform and saturated aqueous sodium hydrogen carbonate and the mixture was stirred at ambient temperature for 30 minutes. The solution was extracted with chloroform and washed with brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to a silica gel column (20g, 5% methanol in chloroform). The solvent was evaporated in vacuo and the residue was solidified with diethyl ether to give 5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1-[2-(4-methyl-1-piperazinyl)ethyl]-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (115 mg).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 30 minutes
  2. extractionThe solution was extracted with chloroform
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ff232e72ef9c4afb9dd7e32860985ea9
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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