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

HRID 1604433Notes

Reaction equation

HRID 1604433 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 5° 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 CHCl3, the solution was dried (MgSO4), and the solvent was removed in vacuo. The residue was crystallized from i-BuCOMe (iso-butylmethylketone) 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 5° C
  2. filtrationthe precipitate was collected by filtration
  3. dry with materialthe solution was dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was crystallized from i-BuCOMe (iso-butylmethylketone)

Sources & evidence

ORD record
ord-bd1b958af90d4e1e8ff3cc397302b6d4
Source dataset
uspto-grants-1999_11
Patent number
US05994372

Reaction notes

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