Ammonia → HCID 18933398, compound

HRID 1598377Notes

Reaction equation

HRID 1598377 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[F:12][C:13]1[CH:33]=[CH:32][C:16]([CH2:17][NH:18][CH:19]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][C:21]#[N:22])=[CH:15][CH:14]=1.N>C(OCC)C>[F:12][C:13]1[CH:33]=[CH:32][C:16]([CH2:17][NH:18][CH:19]([CH2:23][O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][CH2:21][NH2:22])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 18933326HCID 18933326, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18933398HCID 18933398, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (136 mg, 3.58 mmol) in diethyl ether (10 ml) was added under ice-cooling conc. sulfuric acid (0.15 ml, 1.5 mmol) and, after stirring for 0.5 hour, a solution of 3-(p-fluorobenzylamino)-6-phenyl-5-oxahexanenitrile (300 mg, 1.01 mmol) in diethyl ether (5 ml) was added dropwise and the mixture was heated under reflux for one hour. After cooling, aqueous ammonia (2 ml) was added under ice-cooling to the reaction mixture and stirred for 2 hours. The reaction mixture was filtered with Celite and the filtrate was distilled off under reduced pressure. The residue was chromatographed using silica gel column to give the title compound as a colorless oily substance from the fraction from methanol-chloroform-aqueous ammonia (90/10/0.5). Yield=82%.

Workup

  1. additionwas added under ice-
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for one hour
  4. temperatureAfter cooling
  5. temperaturecooling to the reaction mixture
  6. stirringstirred for 2 hours
  7. filtrationThe reaction mixture was filtered with Celite
  8. distillationthe filtrate was distilled off under reduced pressure
  9. customThe residue was chromatographed

Sources & evidence

ORD record
ord-df766da28c99445a93a47f191bb56a8c
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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