Dimethylformamide → HCID 59222472, compound

Temperature

60 °C

The starting material 4-aminomethyl-3-chloro-benzylamine was prepared from 1,4-bis-bromomethyl-2-chloro-benzene as follows. A suspension of 1,4-bis-bromomethyl-2-chloro-benzene (470 mg) and sodiumazide (225 mg) in dimethylformamide (2.5 ml) was stirred at 60° C. for 2 hours. The reaction mixture was then diluted with water and extracted with ether. The combined organic extracts were then washed with water, dried (Na2SO4) and evaporated. Part of the remaining residue (233 mg) was dissolved in methanol (5 ml) and tin(II) chloride (962 mg) was added portionwise at 0° C. The reaction mixture was then stirred at room temperature over night. The solvent was removed and the residue was dissolved in 3N sodium hydroxide (12 ml) and this solution was saturated with sodium chloride and extracted with chloroform. The combined extracts were dried (sodium sulfate) and evaporated and the remaining material was purified by chromatography (dichloromethane/methanol/ammonia 19:1:0.1 and 9:0.9:0.1). 4-Aminomethyl-3-chloro-benzylamine was obtained as light yellow oil (76 mg).

1. extractionextracted with ether
2. washThe combined organic extracts were then washed with water
3. dry with materialdried (Na2SO4)
4. customevaporated
5. dissolutionPart of the remaining residue (233 mg) was dissolved in methanol (5 ml)
6. additiontin(II) chloride (962 mg) was added portionwise at 0° C
7. stirringThe reaction mixture was then stirred at room temperature over night
8. customThe solvent was removed
9. dissolutionthe residue was dissolved in 3N sodium hydroxide (12 ml)
10. extractionextracted with chloroform
11. dry with materialThe combined extracts were dried (sodium sulfate)
12. customevaporated
13. customthe remaining material was purified by chromatography (dichloromethane/methanol/ammonia 19:1:0.1 and 9:0.9:0.1)

ORD record

ord-cb4eb737cfa0491a98a2cf8d1aa36227

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964633B2