4-Methoxybenzylamine → HCID 68289029, compound

HRID 541237Notes

Reaction equation

HRID 541237 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:14]3[CH:10]2[C:11](=[O:16])O[C:13]3=[O:15])=[CH:5][CH:4]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH2:26])=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:11](=[O:16])[CH:10]3[CH:14]([CH:9]3[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:13]2=[O:15])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 86672526HCID 86672526, compound

Product 1

HCID 68289029HCID 68289029, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-(4-Methoxyphenyl)-3-oxabicyclo[3.1.0]hexane-2,4-dione (crude product from the previous step) and (4-methoxyphenyl)methanamine was heated at 180° C. for 1.5 h. After cooling to room temperature, the reaction mixture was dissolved in CH2Cl2 and purified by flash column chromatography with EtOAc in hexane (20%, 30%, then 40%) to give the title compound as a yellow solid (0.71 g, 63% yield over three steps). MS [M+H]+: 338.

Workup

  1. temperatureAfter cooling to room temperature
  2. custompurified by flash column chromatography with EtOAc in hexane (20%, 30%

Sources & evidence

ORD record
ord-4543e7ca11ae489baa9f2a113486a873
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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