Benzyl Bromide → HCID 70167131, compound

HRID 2188214Notes

Reaction equation

HRID 2188214 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:8](NC)[CH2:7][CH2:6]2.C([N:23]([CH2:26][CH3:27])[CH2:24]C)C.C(Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O>[CH2:27]([CH2:26][NH:23][CH2:24][C@H:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C@H:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 57188019HCID 57188019, compound

Product 1

HCID 70167131HCID 70167131, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of cis-6-methoxy-2-methylamino-1-phenyl-1,2,3,4-tetrahydronaphthalene (3.55 g, prepared according to Process 1), triethylamine (3.12 cm3) and N,N-dimethylformamide (40 cm3) was added benzyl bromide (1.60 cm3). The mixture was warmed to 80° C. and stirred for 2 h. Upon cooling, the solvent was evaporated under reduced pressure to afford a brown oil. This was purified by column chromatography [silica, eluting with petroleum ether (b. p. 40-60° C.)-ethyl acetate (4:1)] to afford the title compound (3.52 g) as a light brown oil which solidified on standing.

Workup

  1. temperatureUpon cooling
  2. customthe solvent was evaporated under reduced pressure
  3. customto afford a brown oil
  4. customThis was purified by column chromatography [silica, eluting with petroleum ether (b. p. 40-60° C.)-ethyl acetate (4:1)]

Sources & evidence

ORD record
ord-57de5bcd20104617a4723b0fde05b7c7
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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