Methylamine → (Bis(4-chlorophenyl)methyl)(methyl)amine

HRID 392824

Reaction equation

HRID 392824 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](Cl)[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:17][NH2:18]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([NH:18][CH3:17])[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 130784,4'-Dichlorobenzhydryl chloride

Product 1

HCID 22660951(Bis(4-chlorophenyl)methyl)(methyl)amineYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4′-dichlorobenzhydryl chloride (3.22 g, 11.85 mmol) in a 1.85 M solution of methylamine in tetrahydrofuran (40 ml) was heated at 125° C. in a pressure vessel for 24 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sodium carbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 8:2) gave 2.12 g (67%) of the title amine as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.57 (3H, s, NCH3), 4.85 (1H, s, CH benzhydryl), 7.0-7.53 (8H, m, aromatics). MS (ESI+) (m/z): 266 (M+H).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with sodium carbonate, brine
  3. dry with materialdried (magnesium sulfate)
  4. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 8:2)

Sources & evidence

ORD record
ord-6d37b2411615427c8fec0ebe4c06b3d7
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Linked notes

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