Benzaldehyde → HCID 2852555, compound

HRID 246820Notes

Reaction equation

HRID 246820 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH2:12].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([NH:12][CH2:11][CH:2]1[O:1][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 150532-Aminomethyl-1,4-benzodioxane

Product 1

HCID 2852555HCID 2852555, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2,3-dihydro-1,4-benzodioxin-2-yl)methylamine (4.13 g), benzaldehyde (2.65 g) and methylene chloride (25 ml) is stirred for 3 hours at room temperature and the methylene chloride removed via evaporation. A solution of the residue in ethanol (30 ml) is hydrogenated at atmospheric pressure and room temperature in the presence of methanesulphonic acid (2.4 g) and 10% palladium on charcoal (0.4 g). After the calculated quantity of hydrogen is consumed (510 ml), the solution is filtered, the ethanol is removed via evaporation, the residue is made alkaline with saturated aqueous potassium carbonate, and the resulting solution is extracted with ether. Evaporation of the dried ether extract yields an oily residue of N-benzyl-(2,3-dihydro-1,4-benzodioxin-2-yl)methylamine (5.9 g).

Workup

  1. customthe methylene chloride removed via evaporation
  2. customis hydrogenated at atmospheric pressure and room temperature in the presence of methanesulphonic acid (2.4 g) and 10% palladium on charcoal (0.4 g)
  3. customAfter the calculated quantity of hydrogen is consumed (510 ml)
  4. filtrationthe solution is filtered
  5. customthe ethanol is removed via evaporation
  6. extractionthe resulting solution is extracted with ether
  7. customEvaporation of the dried ether
  8. extractionextract

Sources & evidence

ORD record
ord-d895fa1219154dfe9978b798b255f813
Source dataset
uspto-grants-1987_11
Patent number
US04704389

Reaction notes

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