Triethylamine → 3-chloro-N-[(6-chloropyridin-3-yl)methyl]propan-1-amine

HRID 552911Notes

Reaction equation

HRID 552911 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.Cl.[Cl:11][CH2:12][CH2:13][CH2:14][NH2:15].C(N(CC)CC)C.[OH-].[Na+]>C(#N)C>[Cl:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:8][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 108227283-chloro-N-[(6-chloropyridin-3-yl)methyl]propan-1-amineYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

16.20 g (100 mmol) of 2-chloro-5-(chloromethyl)pyridine, 16.90 g (130 mmol) of 3-chloropropan-1-amine hydrochloride and 36.24 ml (260 mmol) of triethylamine in 200 ml acetonitrile stirred at 60° C. for 20 hours. After addition of 30.67 g (230 mmol) of 30 percent strength aqueous sodium hydroxide solution, the reaction mixture is concentrated under reduced pressure and the residue is extracted with chloroform. Concentration of the extract under reduced pressure gives 19.03 g (87% of theory) of 3-chloro-N-[(6-chloropyridin-3-yl)methyl]propan-1-amine which can be used without further purification for the next reaction (cf. Ex. II-2).

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. extractionthe residue is extracted with chloroform
  3. extractionConcentration of the extract under reduced pressure

Sources & evidence

ORD record
ord-8221b2b2d79d4af5bf8390b1991ca2c1
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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