Benzylamine → (+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-[(phenylmethyl)amino]benzeneacetamide

HRID 465645Notes

Reaction equation

HRID 465645 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:23])[CH:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:3].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:23])[CH:15]([NH:31][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:3]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 19874874(+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-bromobenzeneacetamide

Product 1

HCID 19874931(+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-[(phenylmethyl)amino]benzeneacetamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (±)-N-[2,6-bis(1-Methylethyl)phenyl]-α-bromobenzeneacetamide (4.3 g, 12 mmol), benzylamine (1.8 g, 18 mmol), and triethylamine (8.0 mL, 57 mmol) in toluene was refluxed (96 hours) then cooled and concentrated in vacuo. The residue was taken up in ethyl acetate (300 mL), washed with water (2×100 mL), with saturated aqueous sodium bicarbonate (1×100 mL), with brine (1×100 mL), then dried (MgSO4) and concentrated to a solid. The solid was recrystallized from ethyl acetate/hexane to yield 3.35 g (72.8%) of the title compound as a white solid, mp 134°-137° C.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated in vacuo
  3. washwashed with water (2×100 mL), with saturated aqueous sodium bicarbonate (1×100 mL), with brine (1×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a solid
  6. customThe solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d32a1480c5094961b7ce00a504365f85
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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