Benzylamine → 11-[3-(Benzylamino)propionyl]-5,11-dihydro-6H-pyrido[2,3-b]-[1,4]benzodiazepin-6-one

HRID 2057383Notes

Reaction equation

HRID 2057383 reaction equation
Cl[CH2:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[NH:9][C:8]2[CH:18]=[CH:19][CH:20]=[N:21][C:7]1=2)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(O)C>[CH2:28]([NH:35][CH2:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[NH:9][C:8]2[CH:18]=[CH:19][CH:20]=[N:21][C:7]1=2)=[O:5])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 1381057111-(3-chloropropionyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 2033201911-[3-(Benzylamino)propionyl]-5,11-dihydro-6H-pyrido[2,3-b]-[1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.0 gm of 11-(3-chloropropionyl)-5,11-dihydro-6H-pyrido [2,3-b]-[1,4]benzodiazepin-6-one, 2.3 gm of sodium carbonate and 4.4 gm of benzylamine were refluxed in 80 ml of ethanol for 4 hours. Then the hot mixture was suction-filtered, the alcohol was distilled off, and the residue was purified on a silica gel column. The evaporation residue of the eluate was recrystallized twice from n-propanol.

Workup

  1. filtrationThen the hot mixture was suction-filtered
  2. distillationthe alcohol was distilled off
  3. customthe residue was purified on a silica gel column
  4. customThe evaporation residue of the eluate was recrystallized twice from n-propanol

Sources & evidence

ORD record
ord-4e5d0f9cc78c43b1a50f54d43309ac5f
Source dataset
uspto-grants-1980_07
Patent number
US04210648

Reaction notes

Loading…