3-Amino-1-propanol → 3-((2-Nitrobenzyl)amino)propan-1-ol

HRID 2237462Notes

Reaction equation

[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][NH2:7])([O-:3])=[O:2].N[CH2:13][CH2:14][CH2:15][OH:16]>CN(C=O)C>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][NH:7][CH2:13][CH2:14][CH2:15][OH:16])([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-nitrobenzyl amine (17 g, 78 mmol) in DMF (50 mL) was cooled to 0° C. and treated dropwise with a solution of 3-amino-1-propanol (50 mL, 0.65 mol) in DMF (150 mL) over 0.5 hours. The reaction mixture was stirred at 0° C. for 1 hour, then warmed to room temperature for 2 hours, and evaporated to a red oil. The crude product residue was purified by flash chromatography (SiO2, 10% 0.5 M NH3-methanol/dichloromethane) to afford 3-[(2-nitrobenzyl)amino]propan-1-ol (16 g, 98%) as a yellow oil:

Workup

temperaturewarmed to room temperature for 2 hours
customevaporated to a red oil
customThe crude product residue was purified by flash chromatography (SiO2, 10% 0.5 M NH3-methanol/dichloromethane)

Sources & evidence

ORD record: ord-dc37695b835749bfa9961a0cdbda2262
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718652B2

Reaction notes

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