Ammonia → HCID 57934063, compound

HRID 1950632Notes

Reaction equation

HRID 1950632 reaction equation
FC(F)(F)S(OC1C=CC=CC=1CC1CCC2C(=CC=C(OC)C=2)C1)(=O)=O.COC1C=CC(CCN)=CC=1.C[O:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][NH:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[CH2:56][CH:57]2[CH2:66][CH2:65][C:64]3[C:59](=[CH:60][CH:61]=[C:62]([O:67]C)[CH:63]=3)[CH2:58]2)=[CH:43][CH:42]=1.N>Br>[OH:40][C:41]1[CH:42]=[CH:43][C:44]([CH2:47][CH2:48][NH:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[CH2:56][CH:57]2[CH2:66][CH2:65][C:64]3[CH:63]=[C:62]([OH:67])[CH:61]=[CH:60][C:59]=3[CH2:58]2)=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 4657O-MethyltyramineHCID 23087537HCID 23087537, compoundHCID 66625762HCID 66625762, compound

Product 1

HCID 57934063HCID 57934063, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Synthesized from 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)phenyl trifluoromethanesulfonate (1.6 g) and 2-(4-methoxyphenyl)ethylamine (0.9 g) according to an analogous synthetic method to Example 116, to the total amount of [2-(4-methoxyphenyl)ethyl][2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)phenyl]amine (crude product) was added 48% hydrobromic acid (30 ml), and the solution was refluxed overnight. To the reaction solution was added concentrated aqueous ammonia, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (1.1 g).

Workup

  1. temperaturethe solution was refluxed overnight
  2. extractionthe solution was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-e97dc0ef54e349f3ba405a9baf9aae4f
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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