Benzaldehyde → HCID 178500463, compound

HRID 400101Notes

Reaction equation

HRID 400101 reaction equation
[ClH:1].[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:5][CH2:4]1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CO.[Ni]>[ClH:1].[CH3:14][O:13][C:11]([CH2:10][CH2:9][C@H:6]1[CH2:5][CH2:4][C@H:3]([NH:2][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7]1)=[O:12]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 178500462HCID 178500462, compound

Product 1

HCID 178500463HCID 178500463, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

8.0 g of methyl 3-(trans-4-aminocyclohexyl)propionate-hydrochloride, 4.3 g of benzaldehyde and 5.0 ml of triethylamine in 150 ml of methanol are hydrogenated with 1.0 g of Raney nickel at 50° C. under a hydrogen pressure of 50 psi for 4 hours. After cooling, the mixture is suction filtered and the filtrate is evaporated down. The residue is divided between ethyl acetate and water, the aqueous phase is adjusted to pH 8-9 with sodium hydroxide solution and extracted with ethyl acetate. The combined ethyl acetate phases are washed with saturated saline solution, dried and evaporated down. The residue is suspended in diethylether and mixed with methanolic hydrochloric acid. The precipitate is suction filtered, washed with diethylether and dried.

Workup

  1. customfor 4 hours
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. customthe filtrate is evaporated down
  5. extractionextracted with ethyl acetate
  6. washThe combined ethyl acetate phases are washed with saturated saline solution
  7. customdried
  8. customevaporated down
  9. additionmixed with methanolic hydrochloric acid
  10. filtrationfiltered
  11. washwashed with diethylether
  12. customdried

Sources & evidence

ORD record
ord-e3fc56a659f142d6813a99e10bf38572
Source dataset
uspto-grants-1998_10
Patent number
US05827849

Reaction notes

Loading…