Methylamine → HCID 68579573, compound

HRID 645418Notes

Reaction equation

HRID 645418 reaction equation
[CH3:1][NH2:2].C([O-])([O-])=O.[Na+].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[CH2:23]Br)=[C:12]([CH2:25]Br)[CH:11]=1>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]2[C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=3[CH2:23][N:2]([CH3:1])[CH2:25][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 10340Sodium CarbonateHCID 35598941,1'-Biphenyl, 4,4'-dibromo-2,2'-bis(bromomethyl)-

Product 1

HCID 68579573HCID 68579573, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeNH2 (4.9 mL, 9.87 mmol) and Na2CO3 (0.349 g, 3.29 mmol) were added to a THF (6.5 mL) solution of 4,4′-dibromo-2,2′-bis(bromomethyl)biphenyl (0.328 g, 0.658 mmol), and the reaction mixture was refluxed for 3 hours. The volatile component was removed in vacuo, and the residue was passed through MCX (CH3OH wash; 2.0 M NH3/CH3OH elution) to afford 3,9-dibromo-6-methyl-6,7-dihydro-5H-dibenzo[c,e]azepine as a white solid (0.24 g). 1H NMR (DMSO-d6, δ=2.50, 500 MHz): 2.31 (s, 3H), 3.24 (s, 4H), 7.47 (d, J=7.9, 2 H), 7.55-7.82 (m, 4H).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customThe volatile component was removed in vacuo
  3. washthe residue was passed through MCX (CH3OH wash; 2.0 M NH3/CH3OH elution)

Sources & evidence

ORD record
ord-929616dee64c4493bb0b30ee4e202fc2
Source dataset
uspto-grants-2010_04
Patent number
US07704992B2

Reaction notes

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