Benzylamine → N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamide

HRID 465655

Reaction equation

HRID 465655 reaction equation
Br[CH2:2][C:3](Br)=[O:4].[CH:6]([C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([CH3:18])[CH3:17])[C:10]=1[NH2:11])([CH3:8])[CH3:7].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(N(CC)CC)C>[CH3:17][CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:9]([CH:6]([CH3:8])[CH3:7])[C:10]=1[NH:11][C:3](=[O:4])[CH2:2][NH:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 32484DiisopropylanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 19764427N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

Bromoacetylbromide (4.5 mL) was added portionwise to a mixture of 8.85 g 2,6-diisopropylaniline and 7.0 mL triethylamine in 300 mL EtoAc at 0° C. Upon completing the addition, excess triethylamine and 5.4 g benzylamine were added and the entire mixture was heated on the steambath for 30 minutes. The reaction mixture was allowed to sit overnight at room temperature, and was then filtered, concentrated, and filtered through silica gel (70-230 mesh) using hexane/EtoAc, 1/1, as eluant. A total of 15.62 g (96%) of the title product was obtained.

Workup

  1. additionwere added
  2. temperaturethe entire mixture was heated on the steambath for 30 minutes
  3. filtrationwas then filtered
  4. concentrationconcentrated
  5. filtrationfiltered through silica gel (70-230 mesh)

Sources & evidence

ORD record
ord-6a16c88ba0b2498c9f6d4e1a74c93659
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Linked notes

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