Methylamine → tert-butyl N-(3-(methylamino)propyl)carbamate

Reaction equation

[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10]Br)([CH3:4])([CH3:3])[CH3:2].[CH3:13][NH2:14].C1COCC1>>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:14][CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 11309987tert-butyl N-(3-(methylamino)propyl)carbamateYield 86%

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.