HCID 21182006, compound → HCID 21182005, compound

HRID 1386471Notes

Reaction equation

HRID 1386471 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[CH3:8]>C(O)(C)C.[Pd]>[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[CH3:8]

Participants

4

Reactant 1

HCID 21182006HCID 21182006, compound

Product 1

HCID 21182005HCID 21182005, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent2×

Procedure

A solution containing 0.40 g (1.23 mmol) of N-[2-(2,6-dimethylphenoxy)ethyl]-N-methyl-2-(4-nitrophenyl)ethylamine (Example 2) in 7 ml of isopropanol is added to a suspension of 0.1 g of 10% palladium-on-carbon catalyst in 7 ml of isopropanol. The suspension is hydrogenated under atmospheric pressure. After completion of the reaction, the catalyst is filtered and washed with isopropanol. The filtrate is evaporated to constant weight under reduced pressure to obtain 0.37 g of the oily base (76%), Rf=0.35 (ethyl acetate/methanol=9:1).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst is filtered
  3. washwashed with isopropanol
  4. customThe filtrate is evaporated to constant weight under reduced pressure

Sources & evidence

ORD record
ord-6fa21936fae548bbb03fea80f30287f7
Source dataset
uspto-grants-2001_07
Patent number
US06265445B1

Reaction notes

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