Water → 2-[N-(3-aminopropyl)-N-(2-chlorobenzyl)amino]pyridine

HRID 464354Notes

Reaction equation

HRID 464354 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17]Cl.O>CS(C)=O>[NH2:3][CH2:4][CH2:5][CH2:6][N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[Cl:14]

Participants

6

Reactant 4

HCID 962WaterHCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 10606924N-(3-aminopropyl)pyridin-2-amine

Product 1

HCID 202073322-[N-(3-aminopropyl)-N-(2-chlorobenzyl)amino]pyridineYield 25.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Sodium hydride (1.32 g) was disolved in DMSO (25 ml) at 70°-75° C. under nitrogen. The solution was cooled and 2-(3-aminopropylamino)pyridine (7.5 g) added at room temperature. 2-Chlorobenzyl chloride (8.86 g) in DMSO (15 ml) was added dropwise maintaining the temperature at 20°-25° C. After standing overnight water (200 ml) was added and the mixture extracted with ether. The ether extracts were washed with 2N hydrochloric acid and after partitioning into ether and chloroform at pH 3.5 and 14, an oil was obtained which was further purified by HPLC (silica gel, dichloromethane then 2% ammoniacal methanol/dichloromethane) to give 2-[N-(3-aminopropyl)-N-(2-chlorobenzyl) amino]pyridine (3.44 g) as an oil.

Workup

  1. temperatureThe solution was cooled
  2. temperaturemaintaining the temperature at 20°-25° C
  3. extractionthe mixture extracted with ether
  4. washThe ether extracts were washed with 2N hydrochloric acid
  5. customafter partitioning into ether and chloroform at pH 3.5 and 14
  6. customan oil was obtained which
  7. customwas further purified by HPLC (silica gel, dichloromethane

Sources & evidence

ORD record
ord-9671850757814cf483e63e1633f2456c
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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