N-Methylaniline → N-(3-bromopropyl)-N-methylaniline

HRID 1053592Notes

Reaction equation

HRID 1053592 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:9][CH2:10][CH2:11][CH2:12]Br.C(N(C(C)C)CC)(C)C>C(#N)C>[Br:9][CH2:10][CH2:11][CH2:12][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 80011,3-DibromopropaneHCID 81531Diisopropylethylamine

Product 1

HCID 61288549N-(3-bromopropyl)-N-methylanilineYield 37.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-methylaniline (1.01 mL, 9.33 mmol) was reacted with 1,3-dibromopropane (0.947 mL, 9.33 mmol) and diisopropylethylamine (2.55 mL, 18.66 mmol) in ACN at 70° C. for 12 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide the intermediate 23a as a yellow oil (0.80 g, 3.52 mmol, 37% yield). HRMS (ESI, positive) m/z calcd. for C10H15NBr [M+H]+: 228.03824, found: 228.03824. 1H NMR (CDCl3, 400 MHz) δ 7.67 (t, J=8.4 Hz, 2H), 6.71 (d, J=8.0 Hz, 2H), 6.617 (t, J=7.2 Hz, 1H), 3.562 (t, J=6.8 Hz, 2H), 3.431 (t, J=7.2 Hz, 2H), 2.878 (s, 3H), 2.072 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eeb6e9f2ccb544708ac36eb9d93c657f
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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