HCID 18789883, compound → HCID 18789917, compound

HRID 1106872Notes

Reaction equation

HRID 1106872 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][N:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH3:12])=[C:6]([N:27]2[CH:31]=[CH:30][CH:29]=[CH:28]2)[CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.CO.[Pd]>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][N:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[CH3:12])=[C:6]([N:27]2[CH:31]=[CH:30][CH:29]=[CH:28]2)[CH:5]=1

Participants

6

Reactant 2

HCID 18789883HCID 18789883, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18789917HCID 18789917, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A portion (0.53 g, 1.25 mmol) of the 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane produced in (3) above was dissolved in 50 ml of a 1:1 solvent system of ethyl acetate and methanol and 10% Pd/C (0.15 g) was slowly added to the solution, which was thereafter stirred at ordinary temperatures for 10 min as hydrogen gas was injected. Thereafter, the reaction mixture was filtered through Celite and the filtrate was evaporated, with the residue being purified by being subjected to column chromatography on silica gel using, as an eluent, ethyl acetate containing methanol (10%). The fractions containing the end product were combined and the solvent was evaporated to yield the end compound 1-[4-amino-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (0.49 g) as a yellow oil.

Workup

  1. additionwas slowly added to the solution, which
  2. filtrationThereafter, the reaction mixture was filtered through Celite
  3. customthe filtrate was evaporated, with the residue
  4. custombeing purified
  5. additionethyl acetate containing methanol (10%)
  6. additionThe fractions containing the end product
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-73f3ecf072024a23b3ec3e71c381b821
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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