Diisopropylethylamine → HCID 71608063, compound

HRID 2044131Notes

Reaction equation

HRID 2044131 reaction equation
[F:1][CH:2]([F:8])[CH2:3][NH:4][CH2:5][CH:6]=[CH2:7].C(N(CC)C(C)C)(C)C.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Cl)=[CH:21][N:20]=1>>[Cl:18][C:19]1[N:20]=[CH:21][C:22]([CH2:25][N:4]([CH2:3][CH:2]([F:8])[F:1])[CH2:5][CH:6]=[CH2:7])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 60923061HCID 60923061, compound

Product 1

HCID 71608063HCID 71608063, compoundYield 100.7%

Conditions

Temperature
70 °C

Procedure

An amount of 16.46 g (0.135 mol) of N-(2,2-difluoroethyl)prop-2-en-1-amine is placed in 31.9 g (0.244 mol) of N,N-diisopropylethylamine and 20 g (0.122 mol) of 2-chloro-5-(chloromethyl)pyridine are introduced at 70° C. The mixture is heated at 70° C. for 16 hours and the excess N,N-diisopropylethylamine is subsequently distilled off. The residue is treated with 100 ml of water and extracted twice with 50 ml of dichloromethane. After drying the combined organic phases over magnesium sulphate, they are filtered through a layer of silica gel and the solvent is removed under vacuum. An amount of 30.3 g (98% content) of N-[(6-chloropyridin-3-yl)methyl]-N-(2,2-difluoroethyl)prop-2-en-1-amine is obtained (corresponds to 97.9% yield).

Workup

  1. distillationthe excess N,N-diisopropylethylamine is subsequently distilled off
  2. additionThe residue is treated with 100 ml of water
  3. extractionextracted twice with 50 ml of dichloromethane
  4. dry with materialAfter drying the combined organic phases over magnesium sulphate, they
  5. filtrationare filtered through a layer of silica gel
  6. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-11403ca21cd04e13aaba9eecdcfe4472
Source dataset
uspto-grants-2013_11
Patent number
US08586756B2

Reaction notes

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