HCID 14403357, compound → HCID 14403385, compound

HRID 1032683Notes

Reaction equation

HRID 1032683 reaction equation
[NH:1]([C:5]1[CH:28]=[CH:27][C:8]([C:9]([N:11]2[CH2:18][CH:17]3[CH2:19][CH:13]([CH2:14][N:15](CC4C=CC=CC=4)[CH2:16]3)[CH2:12]2)=[O:10])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[H][H]>CO.[Pd]>[NH:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][NH:15][CH2:14]3)[CH2:18]2)=[O:10])=[CH:27][CH:28]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 2

HCID 14403357HCID 14403357, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14403385HCID 14403385, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

78.0 g (0.21 mole) of 3-(4-acetaminobenzoyl)-7-benzyl-3,7-diazabicyclo[3.3.1]nonane (cf. Example 1) were dissolved in 1.3 l of methanol, and 3.0 g of 10% strength palladium/carbon were added. Hydrogenation was carried out until an equimolar amount of hydrogen had been consumed. The reaction mixture was filtered and the filtrate was evaporated down under reduced pressure. Crystalline 3-(4-acetaminobenzoyl)-3,7-diazabicyclo[3.3.1]nonane was obtained. Yield: 59 g, mp.: 186°-189° C.

Workup

  1. customhad been consumed
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated down under reduced pressure

Sources & evidence

ORD record
ord-bd8453705a274712ab889cbc90fc1c94
Source dataset
uspto-grants-1990_09
Patent number
US04959373

Reaction notes

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