Thiophene → [3-(4-Amino-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester

HRID 390237Notes

Reaction equation

HRID 390237 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([CH2:27][NH:28][CH2:29][CH2:30][CH3:31])[CH:19]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1C=CC=C1.O=[Si]=O>C1COCC1.[Pt]>[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([CH2:27][NH:28][CH2:29][CH2:30][CH3:31])[CH:19]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 24261SilicaHCID 58625058[3-(4-Nitro-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester

Product 1

HCID 58625165[3-(4-Amino-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(4-nitro-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester (0.033 mol) in THF (200 mL) was hydrogenated with 10% Pt/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 through Dicalite, and the filtrate was evaporated. The residue was purified by column chromatography (eluent: 90:10 CH2Cl2:(CH3OH:NH3)). The product fractions were collected, and the solvent was evaporated to yield the title compound as an oil.

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was purified by column chromatography (eluent: 90:10 CH2Cl2:(CH3OH:NH3))
  3. customThe product fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-84c651b12139477d960d36bb4556000f
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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