Benzyl Bromide → Benzonitrile, 4-[bis(phenylmethyl)amino]-

HRID 1777712Notes

Reaction equation

HRID 1777712 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[CH:18][CH:17]=1>CN(C=O)C>[CH2:22]([N:1]([CH2:6][C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1)[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:19]1[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 133964-Aminobenzonitrile

Product 1

HCID 11380991Benzonitrile, 4-[bis(phenylmethyl)amino]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-aminobenzonitrile (1.0 g, 8.47 mmol, 1 eq), K2CO3 (5.85 g, 42.4 mmol, 5.0 eq) and KI (422 mg, 2.54 mmol, 0.3 eq) in dry DMF (10 mL) was added dropwise BnBr (4.0 mL, 33.9 mmol, 4.0 eq) under Ar(g). The reaction mixture was stirred at rt overnight, and was then partitioned with H2O (30 mL), and subsequently extracted with EtOAc (5×20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (9:1-4:1) to furnish the product, 2, as a pale yellow solid (970 mg, 38%).

Workup

  1. customwas then partitioned with H2O (30 mL)
  2. extractionsubsequently extracted with EtOAc (5×20 mL) and CH2Cl2 (20 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe residue was further purified by silica gel column chromatography with hexane/EtOAc (9:1-4:1)
  6. customto furnish the product, 2

Sources & evidence

ORD record
ord-ff4a0d77dca24d5889547f421fbddb1b
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

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