[(Diphenylmethylene)amino]acetonitrile → 2-(Benzhydrylideneamino)-3-quinolin-4-yl-propionitrile

HRID 1597360Notes

Reaction equation

HRID 1597360 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH2:9][C:10]#[N:11])=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.Cl[CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[CH:30][CH:29]=1>C1COCC1>[C:7](=[N:8][CH:9]([CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[CH:30][CH:29]=1)[C:10]#[N:11])([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 612957[(Diphenylmethylene)amino]acetonitrileHCID 2724682Lithium diisopropylamideHCID 123557014-(Chloromethyl)quinoline

Product 1

HCID 234992122-(Benzhydrylideneamino)-3-quinolin-4-yl-propionitrileYield 26.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To N-(Diphenylmethylene)aminoacetonitrile (0.360 g, 1.633 mmol) in 10 ml of anhydrous THF and HMPA (hexamethyl phosphoramidite) (0.38 ml, 2.12 mmol), at −78° C., LDA (2.0 M, 1.06 ml, 2.12 mmol) was added dropwise over a period of 5 minutes. The color of solution turns from colorless to yellow to dark brown. It was then stirred at −78° C. for one hour. 4-Chloromethylquinoline (0.29 g, 1.63 mmol) was added dropwise over a period of 5 minutes and the reaction mixture was slowly brought to room temperature over a period of five minutes. The reaction mixture was quenched by addition of ice and partitioned between EtOAc (20 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered concentrated and column purified (hexanes:EtOAc; 3.5:1.5) to give 0.155 g (26%) of the product as a syrup, which was used as such for the subsequent step.

Workup

  1. waitthe reaction mixture was slowly brought to room temperature over a period of five minutes
  2. customThe reaction mixture was quenched by addition of ice
  3. custompartitioned between EtOAc (20 ml) and water (5 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customcolumn purified (hexanes:EtOAc; 3.5:1.5)

Sources & evidence

ORD record
ord-cf3a69b1f80e4f7ea1ad55e5ec84ae6a
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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