Diphenylacetonitrile → Didiavalo

HRID 726793Notes

Reaction equation

HRID 726793 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[CH:19](Cl)[CH2:20][N:21]([CH3:23])[CH3:22].Cl.O1CCC[CH2:27]1>>[C:12]1([C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)([CH2:19][CH:20]([N:21]([CH3:23])[CH3:22])[CH3:27])[C:10]#[N:11])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 6837DiphenylacetonitrileHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 942942-Chloropropyldimethylamine hydrochloride

Product 1

HCID 31331Didiavalo

Procedure

Sodium hydride (19.5 g of an 80% dispersion in oil, 0.65 mol) was added to a 1 L 3-neck round bottom flask and triturated twice with hexane (150 mL) to remove the oil). Tetrahydrofuran (THF)(150 mL) was added to the flask followed by a stir bar and the resulting suspension stirred under argon whilst adding a solution of diphenylacetonitrile (58 g, 0.3 mol) in THF (150 mL) dropwise via a dropping funnel over 40 minutes. It became necessary to cool the flask in a cold water bath during the addition due to the exotherm generated. After stirring a further 10 minutes at room temperature the flask was fitted with a reflux condenser and placed in an ice bath. The resulting green suspension was then treated with 2-dimethylaminoisopropyl chloride hydrochloride (54 g, 0.34 mol) portionwise, via an addition funnel, over 15 minutes with stirring.

Workup

  1. customtriturated twice with hexane (150 mL)
  2. customto remove the oil)
  3. additionTetrahydrofuran (THF)(150 mL) was added to the flask
  4. customfollowed by a stir bar
  5. temperatureto cool the flask in a cold water bath
  6. additionduring the addition due to the exotherm
  7. stirringAfter stirring a further 10 minutes at room temperature the flask
  8. customwas fitted with a reflux condenser
  9. customplaced in an ice bath
  10. stirringvia an addition funnel, over 15 minutes with stirring

Sources & evidence

ORD record
ord-b48c76636c454d3394433662536d39a4
Source dataset
uspto-grants-1998_01
Patent number
US05710256

Reaction notes

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