Acetonitrile → HCID 71735678, compound

HRID 1053584Notes

Reaction equation

HRID 1053584 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.[CH2:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C.C(#N)C>>[CH3:15][N:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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

4

Reactant 3

HCID 6342AcetonitrileHCID 7670N-EthylanilineHCID 70473457HCID 70473457, compound

Product 1

HCID 71735678HCID 71735678, compoundYield 12.3%

Conditions

Temperature
60 °C

Procedure

To a solution of compound 14a (150 mg, 0.57 mmol) and N-ethylaniline (0.07 mL, 0.63 mmol) in acetonitrile (5.0 mL) diisopropylethylamine (0.24 mL, 1.73 mmol) was added dropwise. After the addition was complete the reaction was stirred at 60° C. for 12 hours. The reaction mixture was concentrated, purified by column chromatography to isolate the required compound 14 as a colorless oil (20 mg, 0.07 mmol, 12% yield). MS (ESI, positive) m/z calcd. for C18H24NO2 [M+H]+: 286.18, found: 285.95. 1H NMR (CDCl3, 400 MHz) δ 7.28 (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), 1.65-1.71 (m, 2H), 1.47-1.55 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-eba9a41d75664b32ac404e59b4122ae2
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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