Ammonia → 11-[4-[2-[(Diethylamino)methyl]-1-piperidinyl]butyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 1084707Notes

Reaction equation

HRID 1084707 reaction equation
[CH2:1]([N:3]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[CH2:13][C:14]#[C:15][CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21](=[O:28])[NH:20][C:19]2[CH:29]=[CH:30][CH:31]=[N:32][C:18]1=2)[CH2:4][CH3:5])[CH3:2].C.[H][H].N>C(O)C.[Pd].ClCCl.C1CCCCC1.CO>[CH2:1]([N:3]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21](=[O:28])[NH:20][C:19]2[CH:29]=[CH:30][CH:31]=[N:32][C:18]1=2)[CH2:4][CH3:5])[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 297MethaneHCID 1455208711-[4-[2-[(Diethylamino)methyl]-1-piperidinyl]but-2-ynyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 1455209511-[4-[2-[(Diethylamino)methyl]-1-piperidinyl]butyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 69163855HCID 69163855, compoundSolvent

Procedure

4.3 g (0.01 mol) of 11-[4-[2-[(diethylamino)methyl]-1-piperidinyl]-but-2-ynyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one were dissolved in 40 ml of ethanol and after the addition of 0.5 g of 10% palladium on animal charcoal the mixture was hydrogenated under 3 bar of hydrogen pressure and at ambient temperature until the uptake of hydrogen had ceased. The mixture was filtered, the filtrate was evaporated down in a water jet vacuum and the oily residue remaining was purified by column chromatography on silica gel (Macherey-Nagel 60, 0.063-0.2 mm) using firstly ethyl acetate, then ethyl acetate/methanol/conc. ammonia 90/10/2 as eluant. From the fractions, after evaporation of the solvent and recrystallisation of the residue from diisopropyl ether, colourless crystals were obtained, m.p. 112° C., RF 0.75 (Merck, ready-made TLC plates, silica gel 60F-254; eluant: dichloromethane/cyclohexane/methanol/conc. ammonia 68/15/15/2 v/v/v/v). Yield: 2.2 g (50.5% of theory).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated down in a water jet vacuum
  3. customthe oily residue remaining was purified by column chromatography on silica gel (Macherey-Nagel 60, 0.063-0.2 mm)
  4. customFrom the fractions, after evaporation of the solvent and recrystallisation of the residue from diisopropyl ether
  5. customcolourless crystals were obtained

Sources & evidence

ORD record
ord-672b079c05b048ac8434840637b3ca05
Source dataset
uspto-grants-1991_04
Patent number
US05006522

Reaction notes

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