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

HRID 23199Notes

Reaction equation

HRID 23199 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-17b4b0c4ef9743189e11324bbc944562
Source dataset
uspto-grants-2005_02
Patent number
US06849739B2

Reaction notes

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