4-Methoxybenzylamine → HCID 57551736, compound

HRID 907257Notes

Reaction equation

HRID 907257 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[C:6](=[O:13])[CH2:5]2.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:21]([CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1)[C:6](=[O:13])[CH2:5]2

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 21782486HCID 21782486, compound2×

Product 1

HCID 57551736HCID 57551736, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 18331056Acetic acid tolueneSolvent

Procedure

A mixture of 6-bromo-isochroman-1,3-dione (0.6 g) (product of step ii)) and 4-methoxybenzylamine (0.313 g) in toluene:acetic acid (4:1, 20 mL) was heated at reflux for 17 hours. The reaction mixture was evaporated and the residue was dissolved in dichloromethane before washing with 2N hydrochloric acid. The organic phase was dried, filtered and evaporated then triturated with diethyl ether to yield the sub-title compound (680 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hours
  3. customThe reaction mixture was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washbefore washing with 2N hydrochloric acid
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customthen triturated with diethyl ether

Sources & evidence

ORD record
ord-9ef914a3e34940759f159420cada6ebc
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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