Propylamine → HCID 21743727, compound

HRID 2187205Notes

Reaction equation

HRID 2187205 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][CH:3]=1.[CH2:10]([NH2:13])[CH2:11][CH3:12]>C(#N)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:13][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 21743727HCID 21743727, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In 15 ml of acetonitrile was dissolved 6.05 g (0.0373 mole) of 6-chloro-3-pyridylmethyl chloride, and under cooling with ice-water and stirring, the solution was added dropwise to a solution of 10.97 g of n-propylamine in 50 ml of acetonitrile. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour and at an external temperature of 50° C. for an additional 1 hour. The acetonitrile was distilled off and the residue was diluted with aqueous sodium hydrogen carbonate solution and extracted with CH2Cl2 (100 ml×3). The extract was dried over MgSO4 and distilled to remove CH2Cl2, whereby 6.94 g of N-(6-chloro-3-pyridylmethyl)-N-n-propylamine was obtained as a yellow-brown oil.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 1 hour and at an external temperature of 50° C. for an additional 1 hour
  3. distillationThe acetonitrile was distilled off
  4. additionthe residue was diluted with aqueous sodium hydrogen carbonate solution
  5. extractionextracted with CH2Cl2 (100 ml×3)
  6. dry with materialThe extract was dried over MgSO4
  7. distillationdistilled
  8. customto remove CH2Cl2

Sources & evidence

ORD record
ord-f9f5bd22a1324915b147106c0bc5c025
Source dataset
uspto-grants-2002_06
Patent number
US06407248B1

Reaction notes

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