Methane → HCID 54001000, compound

HRID 1681819Notes

Reaction equation

HRID 1681819 reaction equation
Cl[C:2]1[C:6]2[N:7]([C:17](=[O:34])[CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:21][CH2:20]3)[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]([CH3:35])[CH:3]=1.C.[OH-].[Na+].C(#N)C>C(O)C.[Pd]>[CH2:32]([N:29]([CH2:30][CH3:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:17]([N:7]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]3[N:4]([CH3:35])[CH:3]=[CH:2][C:6]2=3)=[O:34])[CH2:20][CH2:21]1)[CH3:33]

Participants

7

Reactant 4

HCID 297MethaneHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 19804210HCID 19804210, compound

Product 1

HCID 54001000HCID 54001000, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3.957 g (8.14 millimol) of 3-chloro-4-[[4-[4-(diethylamino)-butyl]-1-piperidinyl]acetyl ]-1-methyl-1,4,9,10-tetrahydropyr rolo[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%), 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 concentrated by evaporation in vacuo, the crystalline hydrochloride 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 recrystallised. 1 g (26.3% of theory) of colourless crystals were obtained, m.p. 198° C. (acetonitrile).

Workup

  1. customat a temperature of 40° C
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated by evaporation 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 recrystallised
  9. custom1 g (26.3% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-e0c06e758adc420fbfae07e6b8726574
Source dataset
uspto-grants-1992_12
Patent number
US05175158

Reaction notes

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