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

HRID 1603731Notes

Reaction equation

HRID 1603731 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-3da913d947c04899a9436a880de8fa1d
Source dataset
uspto-grants-1999_11
Patent number
US05990128

Reaction notes

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