Chloroacetamide → 2-[[2-[3-(3-Fluoro-benzyloxy)-phenyl]-ethyl]-(furan-2-ylmethyl)amino]-acetamide

HRID 1092391Notes

Reaction equation

HRID 1092391 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][NH:15][CH2:16][C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH:10]=[CH:11][CH:12]=1.Cl[CH2:26][C:27]([NH2:29])=[O:28].C(N(CC)CC)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][N:15]([CH2:16][C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH2:26][C:27]([NH2:29])=[O:28])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 8471TriethylamineHCID 59596837HCID 59596837, compound

Product 1

HCID 250166842-[[2-[3-(3-Fluoro-benzyloxy)-phenyl]-ethyl]-(furan-2-ylmethyl)amino]-acetamideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.8 g (5.53 mmol) of [2-[3-(3-fluoro-benzyloxy)-phenyl]-ethyl]-(furan-2-ylmethyl)amine, 0.57 g (6.08 mmol) of 2-chloro-acetamide and 0.92 ml (6.62 mmol) of triethylamine in 5 ml of dry dimethylformamide was heated at 120° C. for 2 hours with microwaves. Solvent was removed under vacuum, water was added and the product was extracted with ethyl acetate. The crude reaction mixture was purified by flash chromatography (dichloromethane/methanol 95:5 v:v). 2.1 g (99% yield) of a yellow oil were isolated.

Workup

  1. customSolvent was removed under vacuum, water
  2. additionwas added
  3. extractionthe product was extracted with ethyl acetate
  4. customThe crude reaction mixture
  5. customwas purified by flash chromatography (dichloromethane/methanol 95:5 v:v)

Sources & evidence

ORD record
ord-d2094d6a13294632867c8d1eedcec49c
Source dataset
uspto-grants-2012_03
Patent number
US08129427B2

Reaction notes

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