Water → 2-[N-(4-aminobutyl)-N-propylamino]pyridine

HRID 2308983Notes

Reaction equation

HRID 2308983 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[CH3:15][CH2:16][CH2:17]I.O>CS(C)=O>[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 14397369N-(4-aminobutyl)pyridin-2-amine

Product 1

HCID 201866172-[N-(4-aminobutyl)-N-propylamino]pyridineYield 66.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

Sodium hydride (1.1 g) was dissolved in DMSO (20 ml) at 70°-75° C. under nitrogen. The solution was cooled and a solution of 2-(4-aminobutylamino)pyridine (6.9 g) in DMSO (20 ml) added at room temperature. N-Propyl iodide (7.81 g) in DMSO (10 ml) was added dropwise maintaining the temperature at 25°-35° C. After a further 15 min. water (200 ml) was added and the mixture was extracted with ether. The ether extract was washed with hydrochloric acid (2N) and the aqueous layer made alkaline to pH 6. After extracting with chloroform, the pH of the aqueous layer was raised to pH 14 and extracted with ether. The ether extracts were washed with 0.1N sodium hydroxide, dried (K2CO3) and the ether evaporated to give 2-[N-(4-aminobutyl)-N-propylamino]pyridine (5.79 g) as an oil which was used without further purification.

Workup

  1. temperatureThe solution was cooled
  2. temperaturemaintaining the temperature at 25°-35° C
  3. extractionthe mixture was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with hydrochloric acid (2N)
  6. extractionAfter extracting with chloroform
  7. temperaturethe pH of the aqueous layer was raised to pH 14
  8. extractionextracted with ether
  9. washThe ether extracts were washed with 0.1N sodium hydroxide
  10. dry with materialdried (K2CO3)
  11. customthe ether evaporated

Sources & evidence

ORD record
ord-f51a7bf93469442da2a723eb9db587d1
Source dataset
uspto-grants-1987_09
Patent number
US04692456

Reaction notes

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