Diisopropylamine → HCID 21801973, compound

HRID 1647828Notes

Reaction equation

HRID 1647828 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21][C:20]2=[O:29])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:30]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[N:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[C:42]([O:41][C:39]([N:30]([CH:21]1[CH2:22][C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]1=[O:29])[NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 97268Di-tert-butyl azodicarboxylateHCID 5076748HCID 5076748, compoundHCID 178418339Butyllithium

Product 1

HCID 21801973HCID 21801973, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.45 g (0.00448 mole) of diisopropylamine dissolved in 20 ml of tetrahydrofuran was added dropwise 2.6 ml (0.00448 mole) of n-butyl lithium (a 1.6M hexane solution) at 0° C., and the mixture was stirred for 20 minutes. After the mixture was cooled to -78° C., to the mixture was added dropwise a solution of 1.00 g (0.00448 mole) of 1-phenyl-3,4-dihydroquinolin-2 (1H)-one dissolved in 10 ml of tetrahydrofuran, and the mixture was stirred at the same temperature for 30 minutes. Next, to the mixture was added dropwise a solution of 2.06 g of di-t-butyl azodicarboxylate dissolved in 10 ml of tetrahydrofuran, and the mixture was stirred at -78° C. for one hour. After completion of the reaction, the reaction mixture was treated with an ammonium chloride aqueous solution, extracted with chloroform and dried over anhydrous sodium sulfate. Chloroform was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane (1:5 v/v)) to obtain 1.41 g of the title compound as a colorless caramel-like product.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. stirringthe mixture was stirred at -78° C. for one hour
  3. customAfter completion of the reaction
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. customChloroform was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane (1:5 v/v))

Sources & evidence

ORD record
ord-bea1d31a06654121af5b4c07b4a465c6
Source dataset
uspto-grants-1995_07
Patent number
US05434148

Reaction notes

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