Benzaldehyde → HCID 24257440, compound

HRID 383988Notes

Reaction equation

HRID 383988 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:10][C:1]1[CH:6]=[C:5]2[C:4]([CH2:7][CH2:8][NH:9][CH:11]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 76751p-Methylphenethylamine

Product 1

HCID 24257440HCID 24257440, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 12.0 g (89 mmol) of 2-p-tolylethylamine and 11.21 ml (111 mmol) of benzaldehyde in PPA (300 g) was heated at 100° C. for 5 days. After cooling to RT it was poured into a saturated aqueous K2CO3 solution (1200 ml). Following the addition of DCM (300 ml) it was stirred for 50 min at RT. Then the phases were separated and the aqueous phase was extracted with DCM (2×500 ml). The organic phases were combined, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 16.3 g of 7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline were obtained as the crude product, which was reacted further with no additional purification.

Workup

  1. temperatureAfter cooling to RT it
  2. customThen the phases were separated
  3. extractionthe aqueous phase was extracted with DCM (2×500 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-b9a9bb53848d473ea0857ee8182b78b8
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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