N-Ethylaniline → HCID 71735928, compound

HRID 1053580Notes

Reaction equation

HRID 1053580 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[CH2:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:15].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:14]([N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:15]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 81531DiisopropylethylamineHCID 12439901HCID 12439901, compound

Product 1

HCID 71735928HCID 71735928, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 12a (250 mg, 1.02 mmol) and N-ethylaniline (0.24 mL, 2.04 mmol) in acetonitrile (5.0 mL), diisopropylethylamine (0.42 mL, 3.05 mmol) was added dropwise. After the addition was complete, the reaction was stirred at 60° C. for 12 hours. The reaction mixture was concentrated and purified by column chromatography to isolate the compound 12 as a colorless oil (20 mg, 0.07 mmol, 12% yield). MS (ESI, positive) m/z calcd. for C18H24NO2 [M+H]+: 286.18, found: 286.18. 1H NMR (400 MHz, Chloroform-d) δ 7.23 (t, J=8 Hz, 1H), 6.65-6.81 (m, 8H), 4.71 (bs, 1H), 3.95 (t, J=5.2 Hz, 2H), 3.33-3.52 (m, 4H), 1.27-1.33 (m, 4H), 1.17 (t, J=6.8 Hz, 3H).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-38936c2e73554b16bce96b17cc9fa7f9
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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