Benzaldehyde → N-Benzyl-6,7-dimethoxy-1-isochromanmethylamine

HRID 259114Notes

Reaction equation

HRID 259114 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][NH2:16])[O:8][CH2:7][CH2:6]2.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1C=CC=CC=1>[CH2:17]([NH:16][CH2:15][CH:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:7][O:8]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 122258846,7-Dimethoxy-1-isochromanmethylamine

Product 1

HCID 21423136N-Benzyl-6,7-dimethoxy-1-isochromanmethylamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 6,7-dimethoxy-1-isochromanmethylamine (18.0 g), benzaldehyde (9.7 g) and dry benzene (400 ml) is heated under reflux (Dean-Stark) for 18 hr. The solvent is removed under reduced pressure and the residue (27.0 g) is dissolved in ethanol (400 ml). Sodium borohydride (17.0 g) is added portionwise to the stirred solution. When the addition is complete the mixture is stirred and heated under reflux for 1.5 hr. and then left at room temperature overnight. The mixture is concentrated, diluted with water and extracted with ether. The ether extracts are in turn extracted with 10% HCl and these extracts are made alkaline and re-extracted with ether. These extracts are washed with brine, dried and evaporated to give the title compound, λmax EtOH 285 nm (3750) and 281 nm (4000).

Workup

  1. temperatureis heated
  2. temperatureunder reflux (Dean-Stark) for 18 hr
  3. customThe solvent is removed under reduced pressure
  4. dissolutionthe residue (27.0 g) is dissolved in ethanol (400 ml)
  5. additionSodium borohydride (17.0 g) is added portionwise to the stirred solution
  6. additionWhen the addition
  7. temperatureheated
  8. temperatureunder reflux for 1.5 hr
  9. concentrationThe mixture is concentrated
  10. additiondiluted with water
  11. extractionextracted with ether
  12. extractionextracted with 10% HCl
  13. extractionre-extracted with ether
  14. washThese extracts are washed with brine
  15. customdried
  16. customevaporated

Sources & evidence

ORD record
ord-c72c271a3f7b4e569a60de32bcf6cc13
Source dataset
uspto-grants-1977_07
Patent number
US04036842

Reaction notes

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