Water → N~1~-[(3-Chlorophenyl)methyl]-N~1~-(pyridin-2-yl)propane-1,3-diamine

HRID 464348Notes

Reaction equation

HRID 464348 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:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]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)[CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([Cl:14])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12103m,alpha-DichlorotolueneHCID 24758Sodium hydrideHCID 10606924N-(3-aminopropyl)pyridin-2-amine

Product 1

HCID 20207360N~1~-[(3-Chlorophenyl)methyl]-N~1~-(pyridin-2-yl)propane-1,3-diamineYield 60.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

Sodium hydride (1.32 g) was dissolved in DMSO (25 ml) at 70°-75° C. under nitrogen. The solution was cooled and 2-(3-aminopropylamino)pyridine (7.56 g) in DMSO (20 ml) added at room temperature. 3-Chlorobenzyl chloride (8.86 g) in DMSO (15 ml) was added dropwise maintaining the temperature at 20°-25° C. After a further 1 hour, water was added (200 ml) and the mixture extracted with ether. The ether extracts were washed with 2N hydrochloric acid and the aqueous layer adjusted to pH 3.5. After extracting with chloroform the pH was raised to 14 and extracted with ether. After drying (K2CO3), the final ether extracts were stripped to give 2-[N-(3-aminopropyl)-N-(3-chlorobenzyl) amino]pyridine (8.34 g) as an oil which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-(3-chlorobenzyl)amino]pyridine (1.65 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (1.3 g) were heated together under reflux in pyridine (15 ml) for 20 hr. On cooling, the mixture was stripped, the residue triturated with wet ether and recrystallised twice from ethanol/water to give 2-[3-[N-(3-chlorobenzyl)-N-pyrid-2-ylamino]propylamino]-5-(6-methylpyrid-3-ylmethyl) pyrimid-4-one 0.6H2O, 1.29 g (53%) mp 100°-104° C.

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. extractionAfter extracting with chloroform the pH
  6. temperaturewas raised to 14
  7. extractionextracted with ether
  8. dry with materialAfter drying (K2CO3)

Sources & evidence

ORD record
ord-b0ba6dd21df543db9943feeb52878bd8
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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