HCID 18793519, compound → HCID 18793513, compound

HRID 1004766Notes

Reaction equation

HRID 1004766 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:21])[CH2:16][NH:17][CH2:18][C:19]#[N:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>N.CO.[Ni]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:21])[CH2:16][NH:17][CH2:18][CH2:19][NH2:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 18793519HCID 18793519, compound

Product 1

HCID 18793513HCID 18793513, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of intermediate 21 (0.0117 mol) in NH3 /CH3OH (60 ml) was hydrogenated at RT with Raney Nickel (2 g) as a catalyst. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated. The residue was treated with a 10% aqueous HCl solution, and this mixture was extracted with ethylacetate. The layers were separated. The aqueous phase was basified, then extracted with ethylacetate. The separated organic layer was dried, filtered, and the solvent was evaporated, yielding 2.71 g (75%) of (±)-N-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]propyl]-1,2-ethanediamine (intermediate 22).

Workup

  1. filtrationAfter uptake of H2, the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe residue was treated with a 10% aqueous HCl solution
  4. extractionthis mixture was extracted with ethylacetate
  5. customThe layers were separated
  6. extractionextracted with ethylacetate
  7. customThe separated organic layer was dried
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5265fe62df464ff780d2ddb925d88ed0
Source dataset
uspto-grants-2000_04
Patent number
US06051718

Reaction notes

Loading…