Benzaldehyde → HCID 18648026, compound

HRID 465666Notes

Reaction equation

HRID 465666 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C1(C)C=CC=CC=1.[Ni]>[CH3:13][CH:12]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:15]([CH3:16])[CH3:17])[C:6]=1[NH:5][C:3](=[O:4])[C@@H:2]([NH:1][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:14]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 22691266HCID 22691266, compound

Product 1

HCID 18648026HCID 18648026, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (S)-α-amino-N-[2,6-bis(1-Methylethyl)phenyl]benzenepropanamide (1.0 g, 3.1 mmol) and benzaldehyde (0.33 g, 3.1 mmol) in toluene (100 mL) was heated under reflux for 1 hour with the azeotropic removal of water then cooled (25° C.). To the resulting solution was added one equivalent of Raney nickel, and the resulting slurry was shaken vigorously under hydrogen (53 psi, 82 min 25° C.). The resulting slurry was filtered, and the filtrate was concentrated. The resulting oil was triturated with ether/hexane (1:1), and the resulting precipitate was collected by filtration to yield 0.27 g (21%) of the title compound, mp 120°-124° C.

Workup

  1. filtrationThe resulting slurry was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting oil was triturated with ether/hexane (1:1)
  4. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-74ee8405fba049239eb872bdb453a6ae
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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