Benzylamine → HCID 20062818, compound

HRID 1084954Notes

Reaction equation

HRID 1084954 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=O)[CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.C(O)C.[Pt]=O>[CH3:15][CH:14]([NH:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:13][CH2:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 20062797HCID 20062797, compound

Product 1

HCID 20062818HCID 20062818, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent2×

Procedure

The product of step (i) (4.16 g) and benzylamine (2.03 g) in toluene (50 ml) was refluxed using a Dean-Stark apparatus for 1 h. The toluene solution in ethanol (100 ml) was hydrogenated over pre-reduced 5% platinum oxide on charcoal (0.40 g). The reaction mixture was filtered (hyflo) and evaporated to give an oil (5.73 g) which was purified by FCC eluting with EA-CX (1:4)+1% TE to give the title compound as a yellow oil (4.51 g). T.l.c. (EA-CX 1:4+few drops TE) Rf 0.11.

Workup

  1. customfor 1 h
  2. filtrationThe reaction mixture was filtered (hyflo)
  3. customevaporated

Sources & evidence

ORD record
ord-57727fc7514d4f8381b15e7ef669ec92
Source dataset
uspto-grants-1991_04
Patent number
US05006556

Reaction notes

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