Hydrochloric Acid → HCID 57437796, compound

HRID 2415136Notes

Reaction equation

HRID 2415136 reaction equation
[C:1]([C:3]1([C:9]([NH2:11])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[ClH:12]>C(O)C.[Pd]>[ClH:12].[NH2:2][CH2:1][C:3]1([C:9]([NH2:11])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 223294021-Cyanocyclohexanecarboxamide

Product 1

HCID 57437796HCID 57437796, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-cyano-cyclohexanecarboxylic acid amide (2.34 g, 20.0 mmol) in ethanol (50 mL) was treated with concentrated HCl (3 mL) and 10% degussa palladium on carbon (0.50 g). The mixture was subjected to hydrogenation conditions (50 psi) for 24 hours, then filtered through Celite. The filtrate was concentrated, then azeotroped with methanol to give a viscous oil. The oil was then resubjected to the above hydrogenation conditions for an additional 20 hours. It was filtered and concentrated as above to give the product (3.85 g, 100%) as a white solid. [M+H]+ 157.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. customazeotroped with methanol
  4. customto give a viscous oil
  5. waitThe oil was then resubjected to the above hydrogenation conditions for an additional 20 hours
  6. filtrationIt was filtered
  7. concentrationconcentrated as above

Sources & evidence

ORD record
ord-35595a26043a4b7e91077e713e6279d9
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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