Formaldehyde → N-[3-(Aminomethyl)phenyl]-N-methylamine

HRID 2070977Notes

Reaction equation

NC1C=C(C=CC=1)CNC(=O)OC(C)(C)C.[CH3:17][NH:18][C:19]1[CH:20]=[C:21]([CH:31]=[CH:32][CH:33]=1)[CH2:22][NH:23]C(=O)OC(C)(C)C.C=O.C([BH3-])#N.[Na+]>>[NH2:23][CH2:22][C:21]1[CH:20]=[C:19]([CH:33]=[CH:32][CH:31]=1)[NH:18][CH3:17]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

HCID 57763264Tert-butyl 3-(methylamino)benzylcarbamate

Product 1

HCID 2760940N-[3-(Aminomethyl)phenyl]-N-methylamine

Procedure

Tert-butyl 3-aminobenzylcarbamate was converted to tert-butyl 3-(methylamino)benzylcarbamate following standard reductive amination conditions using formaldehyde and sodium cyanoborohydride. 3-(aminomethyl)-N-methylaniline was then generated by removal of the Boc protecting group by treatment with HCl (in methanol or dioxane) or trifluoroacetic acid in dichloromethane.

Workup

custom3-(aminomethyl)-N-methylaniline was then generated by removal of the Boc protecting group by treatment with HCl (in methanol or dioxane) or trifluoroacetic acid in dichloromethane

Sources & evidence

ORD record: ord-0aca1f357e754aebb5652c1c94153a63
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

Loading…