Benzaldehyde → HCID 178500463, compound

HRID 976256Notes

Reaction equation

HRID 976256 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)propionatehydrochloride, 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-977e3afc222d43c395980b84c51a2a60
Source dataset
uspto-grants-1997_03
Patent number
US05612335

Reaction notes

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