N-Methylaniline → HCID 71735678, compound

HRID 1053582Notes

Reaction equation

HRID 1053582 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[CH3:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:15][N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 81531DiisopropylethylamineHCID 70473457HCID 70473457, compound

Product 1

HCID 71735678HCID 71735678, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Compound 13a (0.15 g, 0.58 mmol) and compound N-methylaniline (0.07 mL, 0.64 mmol) were stirred in acetonitrile (5 mL) for 30 mins and then diisopropylethylamine (0.24 mL, 1.74 mmol) was added dropwise. The reaction was then stirred at 60° C. for 12 hours and monitored by TLC. The reaction mixture was concentrated and purified by column chromatography to isolate the compound 13 as a colorless oil (0.05 g, 0.36 mmol, 30% yield). MS (ESI, positive) m/z calcd. for C18H24NO2 [M+H]+: 286.18, found: 285.95. 1H NMR (CDCl3, 400 MHz) δ 7.25 (t, J=8.8 Hz, 2H), 6.70-6.85 (m, 7H), 4.72 (s, 1H), 3.93 (t, J=6.4 Hz, 2H), 3.36 (t, J=7.6 Hz, 2H), 2.95 (s, 3H), 1.85-1.78 (m, 2H), 1.63-1.71 (m, 2H), 1.47-1.55 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-807a9e03267e4eed866eb9bb830dcd03
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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