N-Methylbenzylamine → N-benzyl-(3-methoxy-4-nitro-benzyl)-methyl-amine

HRID 1821798Notes

Reaction equation

HRID 1821798 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[CH2:15]Br>>[CH2:3]([N:2]([CH3:1])[CH2:15][C:14]1[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:12]([O:11][CH3:10])[CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 7669N-MethylbenzylamineHCID 126216043-Methoxy-4-nitrobenzyl bromide

Product 1

HCID 22046408N-benzyl-(3-methoxy-4-nitro-benzyl)-methyl-amine

Procedure

A solution of N-methyl-benzyl amine was alkylated with 3-methoxy-4-nitro-benzyl bromide as described above for compound 338. 1H NMR (400 MHz, CDCl3): δ 7.83 (d, J=8.6 Hz, 1H), 7.35 (s, 4H), 7.26 (s, 1H), 7.17 (s, 1H), 7.01 (d, J=7.04 Hz, 1H), 3.97 (s, 3H), 3.55 (s, 4H), 2.22 (s, 3H).

Sources & evidence

ORD record
ord-45585fb2b478427d9d8a5727bb47c611
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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