Triethylamine → N-benzyl-2-bromo-N-propan-2-ylacetamide

HRID 900119Notes

Reaction equation

HRID 900119 reaction equation
[CH:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:3])[CH3:2].CCN(CC)CC.[Br:19][CH2:20][C:21](Br)=[O:22]>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:21](=[O:22])[CH2:20][Br:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 66024Isopropylbenzylamine

Product 1

HCID 15216006N-benzyl-2-bromo-N-propan-2-ylacetamideYield 80.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-isopropylbenzylamine (40 mL, 240 mmol) in CHCl3 (300 mL) was added Et3N (36.8 mL). The reaction was cooled to 0° C. and bromoacetyl bromide (21.8 mL, 251 mmol) was added. The mixture was stirred at room temperature for 24 hours and was diluted with CH2Cl2. The organic solution was washed consecutively with 5% aqueous HCl (1×) and aqueous NaHCO3 (1×). The organic solution was dried (Na2SO4), filtered and concentrated. The residue was dissolved in 40% EtOAc in hexanes and was filtered through a silica gel pad to provide 52.2 g of N-benzyl-2-bromo-N-isopropyl-acetamide. 1H NMR (CD2Cl2) δ 7.20-7.40 (m, 5H), 4.53 (d, 2H), 4.22 (m) and 4.74 (m, total 1H), 4.01 (s, 1H), 3.72 (s, 1H), 1.20 (d, 3H), 1.12 (d, 3H).

Workup

  1. washThe organic solution was washed consecutively with 5% aqueous HCl (1×) and aqueous NaHCO3 (1×)
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 40% EtOAc in hexanes
  6. filtrationwas filtered through a silica gel pad

Sources & evidence

ORD record
ord-be2a0348956c411e8867072fdfbb2500
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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