p-Toluenesulfonic acid → HCID 14493457, compound

HRID 2099578Notes

Reaction equation

HRID 2099578 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C-:28]#[N:29].[K+]>O>[C:28]([CH:6]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2])#[N:29]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 9032Potassium CyanideHCID 90670m-Formylbenzonitrile

Product 1

HCID 14493457HCID 14493457, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-cyanobenzaldehyde (8.0 g, 61.0 mmol) was added morpholine (10.63 g, 122.0 mmol), p-toluenesulfonic acid (12.18 g, 64.05 mmol), and then a solution of potassium cyanide (3.97 g, 61.0 mmol) in 12mL water. The mixture was refluxed for 75 minutes then cooled to room temperature and partitioned between satd. sodium bicarbonate and methylene chloride. The aqueous portion was extracted with methylene chloride (1×), and the resulting organic portion washed with satd. sodium bisulfite (1×). The organic portion was dried over sodium sulfate and concentrated in vacuo. Crystallization from hot ethanol gave 3-[cyano(morpholin-4-yl)methyl]benzonitrile (11.83 g, 85%). LRMS m/z (M+H) Calcd: 228.3, found: 228.1.

Workup

  1. temperatureThe mixture was refluxed for 75 minutes
  2. custompartitioned between satd
  3. extractionThe aqueous portion was extracted with methylene chloride (1×)
  4. washthe resulting organic portion washed with satd
  5. dry with materialThe organic portion was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customCrystallization from hot ethanol

Sources & evidence

ORD record
ord-c261341347464d6cad31c34147a7c6ee
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

Loading…