tert-butyl N-[3-(methylamino)propyl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (3-Methylamino-propyl)-carbamic acid tert-butyl ester (7.00 g, 36.8 mmol) and 3,5-dichloro-[1,2,4]thiadiazole (4.75 g, 30.7 mmol) were dissolved in DMSO (150 mL). Finally, triethylamine (3 mL) was added and the reaction mixture was stirred at room temperature for 24 h. After this period, brine (100 mL) was poured into the reaction vessel and the mixture was transferred to a separatory funnel. The resulting layer was extracted with DCM (3×300 mL). The DCM layer was then dried over anhydrous Na2SO4. The crude product was purified using flash silica chromatography (DCM to 9:1 DCM/MeOH) to afford 6.5 g (69%) of {3-[(3-chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester as a clear oil. [M+H]+ 307.40. After this period the mixture was transferred to a separatory funnel The resulting layer was extracted with DCM (3×300 mL) The DCM layer was then dried over anhydrous Na2SO4 The crude product was purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (3-Bromo-propyl)-carbamic acid tert-butyl ester (11.2 g, 47.0 mmol) was combined with 2.0 M Methylamine in THF (100 mL, 200 mmol) and was stirred at room temperature for 4 h. After this period, a precipitate formed in the solution. The solution was filtered and concentrated under reduced pressure to yield 7.58 g (86%) of (3-methylamino-propyl)-carbamic acid tert-butyl ester as a clear oil. [M+H]+ 188.94. After this period a precipitate formed in the solution The solution was filtered concentrated under reduced pressure