Benzyl Bromide → 2-[N-(3-aminopropyl)-N-benzylamino)pyridine

HRID 464346Notes

Reaction equation

HRID 464346 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.[H][H].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CS(C)=O.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)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10606924N-(3-aminopropyl)pyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 201503642-[N-(3-aminopropyl)-N-benzylamino)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of sodium hydride (0.7 g) and 2-(3-aminopropylamino)pyridine (4.02 g) in DMSO (25 ml) was heated slowly to 75° C. under nitrogen. After the evolution of hydrogen had ceased the solution was cooled to room temperature and benzyl bromide (3.17 ml) added dropwise below 35° C. After a further 30 minutes water was added and the mixture extracted with chloroform. The chloroform extracts were washed with 2N hydrochloric acid, the pH of the aqueous layers ajusted to 4.5 and re-extracted with chloroform. The pH was further raised to 14 and again extracted with chloroform. After drying (K2CO3), the final chloroform extract, on stripping, afforded 2-[N-(3-aminopropyl)-N-benzylamino]pyridine as an oil (3.91 g) which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-benzylamino]pyridine (1.64 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (1.48 g) were heated together under reflux in pyridine (15 ml) for 20 hr. After stripping the residue was treated with wet ether and the resulting solid recrystallised from ethanol/water to give 2-[3-(N-benzyl-N-pyrid-2-ylamino)propylamino]-5-(6-methylpyrid-3-ylmethyl)-pyrimid-4-one 0.75H2O, 1.46 g (56%) mp 90°-96° C.

Workup

  1. temperaturewas cooled to room temperature
  2. extractionthe mixture extracted with chloroform
  3. washThe chloroform extracts were washed with 2N hydrochloric acid
  4. extractionre-extracted with chloroform
  5. temperatureThe pH was further raised to 14
  6. extractionagain extracted with chloroform
  7. dry with materialAfter drying (K2CO3)
  8. extractionthe final chloroform extract, on stripping

Sources & evidence

ORD record
ord-c3972206724e460096f4898df804d0c7
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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