Benzyl Bromide → 6H-Pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-(1-oxo-3-(4-(phenylmethyl)-1-piperazinyl)propyl)-

HRID 2057906Notes

Reaction equation

HRID 2057906 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[C:15](=[O:22])[NH:14][C:13]3[CH:23]=[CH:24][CH:25]=[N:26][C:12]2=3)=[O:10])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)C>[CH2:33]([N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][C:9]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[C:15](=[O:22])[NH:14][C:13]3[CH:23]=[CH:24][CH:25]=[N:26][C:12]2=3)=[O:10])[CH2:2][CH2:3]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 203293835,11-dihydro-11-[3-(1-piperazinyl)-propionyl]-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one

Product 1

HCID 30532046H-Pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-(1-oxo-3-(4-(phenylmethyl)-1-piperazinyl)propyl)-Yield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.51 g of 5,11-dihydro-11-[3-(1-piperazinyl)-propionyl]-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one and 1.6 g of sodium carbonate were added to the mixture of 2.14 g of benzylbromide in 100 ml of absolute ethanol and the mixture was refluxed for 6 hours. Then, the hot mixture was vacuum filtered and the filtrate was evaporated to dryness in vacuo and purified by a silica gel column. The residue of the eluent was then crystallized from xylene to obtain a 42% yield of 11-[3-(4-benzyl-1-piperazinyl)-propionyl]-5,11-dihydro-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one melting at 205°-207° C.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. filtrationfiltered
  3. customthe filtrate was evaporated to dryness in vacuo
  4. custompurified by a silica gel column
  5. customThe residue of the eluent was then crystallized from xylene

Sources & evidence

ORD record
ord-3b5f0176d3dd4684b72c8b1c76819fe5
Source dataset
uspto-grants-1980_07
Patent number
US04213985

Reaction notes

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