Methane → 4-[[[2-[2-[(Dipropylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-1-methyl-1,4,9,10-tetrahydro-pyrrolo[3,2-b][1,5]benzodiazepin-10-one

HRID 2351412Notes

Reaction equation

HRID 2351412 reaction equation
Cl[C:2]1[C:6]2[N:7]([C:17]([NH:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]3[CH2:28][N:29]([CH2:33][CH2:34][CH3:35])[CH2:30][CH2:31][CH3:32])=[O:18])[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[N:4]([CH3:36])[CH:3]=1.C.[OH-].[Na+]>C(O)C.[Pd]>[CH2:30]([N:29]([CH2:28][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][N:22]1[CH2:21][CH2:20][NH:19][C:17]([N:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[NH:10][C:11](=[O:12])[C:5]2[N:4]([CH3:36])[CH:3]=[CH:2][C:6]1=2)=[O:18])[CH2:33][CH2:34][CH3:35])[CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 142100783-Chloro-4-[[[2-[2-[(dipropylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-1-methyl-1,4,9,10-tetrahydro-pyrrolo[3,2-b][1,5]benzodiazepin-10-one

Product 1

HCID 142100794-[[[2-[2-[(Dipropylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-1-methyl-1,4,9,10-tetrahydro-pyrrolo[3,2-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4.2 g (8.15 mol) of 3-chloro-4-[[[2-[2-[(dipropylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-1-methyl-1,4,9,10-tetrahydro-pyrrolo[3,2-b][1,5]benzodiazepin-10-one were dissolved in 350 ml of hot ethanol and after the addition of 3 g of palladium on animal charcoal (20%), the mixture was hydrogenated for 20 hours under a hydrogen pressure of 50 bar and at a temperature of 40° C. The catalyst was filtered off, the filtrate was evaporated down in vacuo, the residue was taken up in 20 ml of water, the solution obtained was made alkaline with sodium hydroxide and extracted exhaustively with dichloromethane. The combined extracts were dried over sodium sulphate and evaporated down and the residue remaining was crystallised once from ethyl acetate and once from acetonitrile. 2.1 g (54% of theory) of colourless crystals were obtained, m.p. 153°-155° C.

Workup

  1. customat a temperature of 40° C
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated down in vacuo
  4. customthe solution obtained
  5. extractionextracted exhaustively with dichloromethane
  6. dry with materialThe combined extracts were dried over sodium sulphate
  7. customevaporated down
  8. customthe residue remaining was crystallised once from ethyl acetate and once from acetonitrile
  9. custom2.1 g (54% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-57eb6f59ef244ed1b9b56db36f0b554f
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

Loading…