O-Methyltyramine → 2-[(4-Methoxyphenethyl)aminomethyl]-1,2,3,4-tetrahydronaphthalene

HRID 1901511Notes

Reaction equation

HRID 1901511 reaction equation
Br[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH2:20][NH2:21])=[CH:17][CH:16]=1>CCO>[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH2:20][NH:21][CH2:2][CH:3]2[CH2:12][CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 4657O-MethyltyramineHCID 127232822-(Bromomethyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 98176402-[(4-Methoxyphenethyl)aminomethyl]-1,2,3,4-tetrahydronaphthaleneYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromomethyl-1,2,3,4-tetrahydronaphthalene (1.33 g, 5.91 mmol) and 4-methoxyphenethylamine (1.79 g, 11.8 mmol) in 50 ml of EtOH was refluxed for 48 hours. After removal of EtOH in vacuo, the residue was dissolved in 100 ml of CHCl3, washed with 10% K2CO3, H2O, sat'd brine, and then dried over Na2SO4. Filtration followed by evaporation of solvent gave a yellow oil, which was purified by chromatography (SiO2, MeOH:CHCl3, 5:95) to a give a yellowish oil (1.03 g, 58.9%). The product was converted to HCl salt, crystallization with MeOH/Et2O gave a white powder. mp 274°-275° C.; Calcd for C20H25NO.HCl: C 72.37, H 7.91, N 4.22; Found C 72.40, H 7.76, N 4.13.

Workup

  1. customAfter removal of EtOH in vacuo
  2. dissolutionthe residue was dissolved in 100 ml of CHCl3
  3. washwashed with 10% K2CO3, H2O
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration
  6. customfollowed by evaporation of solvent
  7. customgave a yellow oil, which
  8. customwas purified by chromatography (SiO2, MeOH:CHCl3, 5:95) to

Sources & evidence

ORD record
ord-194392b1d8fe4d6089ff9cfe19191748
Source dataset
uspto-grants-1996_11
Patent number
US05578611

Reaction notes

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