Triethylamine → HCID 19874877, compound

HRID 465647Notes

Reaction equation

HRID 465647 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:18])[CH:15](Br)[CH3:16])[CH3:3].[C:19]1([CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][NH2:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[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:18])[CH:15]([NH:27][CH2:26][CH:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:16])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 775752,2-DiphenylethylamineHCID 19874944HCID 19874944, compound

Product 1

HCID 19874877HCID 19874877, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (±)-N-[2,6-bis(1-Methylethyl)-phenyl]-2-bromopropanamide (2.0 g, 6.4 mmol), 2,2-diphenylethylamine (1.26 g, 6.41 mmol) and triethylamine (1.8 mL, 13 mmol) in acetonitrile (30 mL) was refluxed (96 hours), then cooled (25° C.). The resulting slurry was diluted with ethyl acetate (300 mL), washed with water (1×100 mL), with saturated aqueous sodium bicarbonate (1×100 mL), with brine (1×100 mL), then dried (MgSO4) and concentrated. Crystallization from ethyl acetate/hexane yielded 2.0 g (72.8%) of the title compound as a white solid, mp 206.5°-208.5° C.

Workup

  1. washwashed with water (1×100 mL), with saturated aqueous sodium bicarbonate (1×100 mL), with brine (1×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9a33d1b5a842462fa8d79b79ad91ac31
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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