Thiophene → 3-(4-Amino-3-propylaminomethyl-phenoxy)-benzonitrile

HRID 390219Notes

Reaction equation

HRID 390219 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:6][C:5]=1[CH2:19][NH:20][CH2:21][CH2:22][CH3:23])([O-])=O.S1C=CC=C1.O=[Si]=O>CO.[Pd]>[NH2:1][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:6][C:5]=1[CH2:19][NH:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 24261SilicaHCID 586250603-(4-Nitro-3-propylaminomethyl-phenoxy)-benzonitrile

Product 1

HCID 586251143-(4-Amino-3-propylaminomethyl-phenoxy)-benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(4-nitro-3-propylaminomethyl-phenoxy)-benzonitrile (0.045 mol) in methanol (250 mL) was hydrogenated with 10% Pd/C (2 g) as a catalyst in the presence of thiophene solution (2 mL). After uptake of H2 gas (3 equiv.), the reaction mixture was filtered over Dicalite and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: 98:2 CH2Cl2:CH3OH). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was purified by column chromatography over silica gel (eluent: 98:2 CH2Cl2:CH3OH)
  3. customThe purest product fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-28cd30170ce94cc887685d672ccdebab
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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