2-Benzyl-5-cyanomethyl-2,5-diazabicyclo[2.2.1]heptane → 2-Benzyl-5-(2-aminoethyl)-2,5-diazabicyclo[2.2.1]heptane

HRID 988956Notes

Reaction equation

HRID 988956 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[CH2:15][C:16]#[N:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].N>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[CH2:15][CH2:16][NH2:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 219636452-Benzyl-5-cyanomethyl-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 219636712-Benzyl-5-(2-aminoethyl)-2,5-diazabicyclo[2.2.1]heptaneYield 85.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A solution of 5.74 g (25.3 mmoles) of 140 and 50 mL of NH3 were hydrogenated with 2 g of Raney nickel in a steel autoclave at 100 bar H2 and 100° C. for 2 hours. The catalyst was filtered off with suction and the solution was evaporated and distilled using a bulb tube (boiling point: 135°-145° C. at 0.01 mbar): 5.02 g of 141 as a colorless oil (87% of the theoretical yield).

Workup

  1. filtrationThe catalyst was filtered off with suction
  2. customthe solution was evaporated
  3. distillationdistilled

Sources & evidence

ORD record
ord-c68908c4903e46c8b58522e109f42e98
Source dataset
uspto-grants-2003_10
Patent number
US06638925B2

Reaction notes

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