Hydrochloric Acid → HCID 17950730, compound

HRID 1420880Notes

Reaction equation

HRID 1420880 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][NH:6][C:7]1([CH3:17])[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8]1)#N.[ClH:18]>C(O)C.[Pd]>[ClH:18].[CH3:17][C:7]1([N:6]2[CH2:5][CH2:4][CH2:3][CH2:1]2)[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18783154HCID 18783154, compound

Product 1

HCID 17950730HCID 17950730, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(3-Cyanopropyl)-1,3,3,5,5-pentamethylcyclohexylamine (2) (1.2 g, 5.1 mmol) in ethanol (120 ml) and conc. HCl (4 ml) was hydrogenated over 10% Pd/C (250 mg) at 7 bar for 40 h (after 24 h additional portion of catalyst (260 mg) was added). The catalyst was removed by filtration through celite pad and solvent evaporated. The residue was treated with acetonitrile, the solids filtered off and the filtrate evaporated. The crude product vas crystallized from ether to give N-(1,3,3,5,5-pentamethylcyclohexyl) pyrrolidine hydrochloride (3) (0.67 g, 49%) with m.p. 156-158° C.

Workup

  1. customThe catalyst was removed by filtration through celite pad and solvent
  2. customevaporated
  3. additionThe residue was treated with acetonitrile
  4. filtrationthe solids filtered off
  5. customthe filtrate evaporated
  6. customThe crude product vas crystallized from ether

Sources & evidence

ORD record
ord-e31801bcf7f44ed38509884409e28d74
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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