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

HRID 1761222Notes

Reaction equation

HRID 1761222 reaction equation
Cl.[CH2:2]([NH2:13])[CH2:3][C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1.C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl>[Cl:21][CH2:22][C:23]([NH:13][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1)=[O:24]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 74246Phenethylamine, 3,4-methylenedioxy-, hydrochloride

Product 1

HCID 22487609N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-chloroacetamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To homopiperonylamine hydrochloride (2.14 g, 10.6 mmol) (a compound of formula (Y7)) in CH2Cl2 (20 mL) in an ice bath was added triethylamine (3.1 mL, 21 mmol) and chloroacetyl chloride (0.85 mL, 10 mmol) (a compound of formula Y6)). After warming to ambient temperature and stirring for 16 hours, the reaction was partitioned with 1 N HCl. The organic layer was separated, washed with aqueous bicarbonate, dried (Na2SO4), and the solvent was removed in vacuo to give 1.8 g of 2-chloro-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide, a compound of formula Y8).

Workup

  1. customthe reaction was partitioned with 1 N HCl
  2. customThe organic layer was separated
  3. washwashed with aqueous bicarbonate
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a3a458043bde42d7b80795eb4797ee2b
Source dataset
uspto-grants-2005_01
Patent number
US06846829B2

Reaction notes

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