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

HRID 983713Notes

Reaction equation

HRID 983713 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-006d7b9671bf4d8fb0636f31182a7a05
Source dataset
uspto-grants-2005_03
Patent number
US06864368B2

Reaction notes

Loading…