Triethylamine → HCID 59199343, compound

HRID 2089523Notes

Reaction equation

HRID 2089523 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][NH:5][CH3:6].C(N(CC)CC)C.[C:18]([O:21][CH2:22][C:23](Cl)=[O:24])(=[O:20])[CH3:19]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][N:5]([CH3:6])[C:23]([CH2:22][O:21][C:18](=[O:20])[CH3:19])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 5223602-Bromo-N-methylbenzylamine

Product 1

HCID 59199343HCID 59199343, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-N-methyl benzylamine (CAS#698-19-1, 0.57 mL, 3.89 mmol) in THF (10 mL) at 0° C. is added triethylamine (0.98 mL, 1.03 mmol) followed by acetoxyacetylchloride (0.63 mL, 5.86 mmol). The reaction is permitted to warm to room temperature and after two hours the reaction is quenched with saturated aqueous NaHCO3 and diluted with ethyl acetate. The layers are separated and the organic layer is dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-hexanes, 1:4 to 3:2) to provide acetic acid [(2-bromo-benzyl)-methyl-carbamoyl]-methyl ester; MS: (ESI) m/z 300.1, 302.1 (M+H)+.

Workup

  1. customis quenched with saturated aqueous NaHCO3
  2. additiondiluted with ethyl acetate
  3. customThe layers are separated
  4. dry with materialthe organic layer is dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-hexanes, 1:4 to 3:2)

Sources & evidence

ORD record
ord-d743fd517b8644db958bb245aef9a194
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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