Chloroacetyl chloride → N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-chloroacetamide

HRID 1170484Notes

Reaction equation

HRID 1170484 reaction equation
Cl.[CH2:2]1[O:13][C:12]2[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH2:9])=[CH:5][C:4]=2[O:3]1.[Cl:14][CH2:15][C:16](Cl)=[O:17]>ClCCCl>[O:13]1[C:12]2[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][NH:9][C:16](=[O:17])[CH2:15][Cl:14])=[CH:5][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 74246Phenethylamine, 3,4-methylenedioxy-, hydrochloride

Product 1

HCID 22487609N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-chloroacetamideYield 27%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3,4-Methylenedioxyphenethylamine hydrochloride (101 mg, 0.5 mmol) was dissolved in DCE (2 mL) and TEA (70 μL). Next, chloroacetyl chloride (48 μL, 0.6 mmol) was added and the reaction was allowed to stir at room temperature for 16 hours. After this time, the solution was concentrated down under N2. The residue was redissolved in DCM, washed with sat. NaHCO3 (aq) and dried over Na2SO4. The crude residue was purified by Prep-LCMS to afford 32 mg (27%) of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-chloro-acetamide. 1H-NMR (400 MHz, CDCl3) δ 6.75-6.62 (m, 3H), 5.92 (s, 2H), 4.01 (s, 2H), 3.52-3.47 (m, 2H), 2.79-2.72 (t, 2H).

Workup

  1. concentrationAfter this time, the solution was concentrated down under N2
  2. dissolutionThe residue was redissolved in DCM
  3. washwashed with sat. NaHCO3 (aq)
  4. dry with materialdried over Na2SO4
  5. customThe crude residue was purified by Prep-LCMS

Sources & evidence

ORD record
ord-2c0ed8085d8a44659e82d6460ec2189b
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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