Ethanol → HCID 10399169, compound

HRID 581069Notes

Reaction equation

HRID 581069 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1[C:16]2[O:15][CH2:14][CH2:13][O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)=[N+]=[N-].[H][H].[CH2:19]([OH:21])[CH3:20]>[Pd]>[O:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:6][CH2:5][CH2:4][NH:1][C:19](=[O:21])[CH3:20])[C:16]=2[O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 702EthanolHCID 54416294HCID 54416294, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10399169HCID 10399169, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The amine is first of all synthesised by catalytic hydrogenation of the compound obtained in Step A. The latter (900 mg; 4.1 mmol) is dissolved with ethanol (15 ml) in the reactor of a Paar apparatus. After the addition of the catalyst, in this case 10% palladium on carbon (90 mg; 10% by weight), stirring is maintained for 4 hours at room temperature at a hydrogen pressure of 45 psi. The reaction mixture is filtered and then concentrated under reduced pressure, and the amine is recovered in the form of a colourless oil. The latter is of the correct purity according to thin-layer chromatography and will thus be acetylated directly under the conditions of Step C of Example 1. Pale yellow oil.

Workup

  1. additionAfter the addition of the catalyst
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated under reduced pressure
  4. customthe amine is recovered in the form of a colourless oil

Sources & evidence

ORD record
ord-fca5ac5b1de54443865bb97b947cfe7e
Source dataset
uspto-grants-1999_07
Patent number
US05919814

Reaction notes

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