Sodium Hydroxide → HCID 18357377, compound

HRID 428337Notes

Reaction equation

HRID 428337 reaction equation
[CH:1]([N:4]([CH:16]([CH3:18])[CH3:17])[CH2:5][CH2:6][CH:7]([C:14]#[N:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[OH-:19].[Na+]>OS(O)(=O)=O>[CH:16]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14](=[O:19])[NH2:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 126122104-Diisopropylamino-2-phenyl-butyronitrile

Product 1

HCID 18357377HCID 18357377, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

N,N-Diisopropyl-3-cyano-3-phenylpropanamine (11.6 g, 47.5 mmol) was mixed with H2SO4 (90%, 100 mL) and the mixture was stirred at 100° C. for 30 min. The reaction mixture was poured on ice, made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were dried (Na2SO4) and the solvent evaporated, affording the title compound as a colourless oil, 12.4 g (100%); 1H NMR (CDCl3) δ1.26 (m, 12H), 2.14 (m, 1H), 2.60 (m, 1H), 2.73 (t, 2H), 3.31 (m, 2H), 3.86 (t, 1H), 6.06 (br, 2H), 7.51-7.61 (m, 5H).

Workup

  1. additionThe reaction mixture was poured on ice
  2. extractionextracted twice with diethyl ether
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-1020e07ef31e409ca2aa273091decfce
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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