Methylamine → N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromide

HRID 1368331Notes

Reaction equation

HRID 1368331 reaction equation
[CH3:1][NH2:2].C([O-])([O-])=O.[Na+].[Na+].[Br:9][CH2:10][CH2:11][C:12]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](Cl)=[O:14]>O.C1(C)C=CC=CC=1>[BrH:9].[C:16]1([C:12]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:11][CH2:10][O:14][C:13]2=[CH:1][NH2:2])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 10340Sodium CarbonateHCID 222500664-Bromo-2,2-diphenylbutyric chloride

Product 1

HCID 70010487N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromideYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a mixture of 35% aqueous methylamine (100 g, 1.13 mol) and Na2CO3 (106 g, 1 mol) in H2O (1000 ml) and toluene (800 ml) was added dropwise 4-bromo-2,2-diphenylbutyroyl chloride (337.5 g, 1.13 mol) in toluene (200 ml), while the temperature was maintained between 0 and 15° C. The mixture was allowed to warm to room temperature and the precipitate was collected by filtration. The solid precipitate was then taken up into CHCl3the solution was dried (MgSO4), and the solvent was removed in vacuo. The residue was crystallized from i-BuCOMe (isobutylmethylketone) to afford pure N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromide (223 g, 67%), mp 159-161° C.

Workup

  1. temperaturewhile the temperature was maintained between 0 and 15° C
  2. filtrationthe precipitate was collected by filtration
  3. dry with materialwas dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was crystallized from i-BuCOMe (isobutylmethylketone)

Sources & evidence

ORD record
ord-6e3b46793c6b4919bf566b0e5cec3466
Source dataset
uspto-grants-2003_06
Patent number
US06573282B1

Reaction notes

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