Dimethylformamide → 4,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrile

HRID 1471015Notes

Reaction equation

HRID 1471015 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=3)[N:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[Cu][C:31]#[N:32].[OH-].[NH4+].[CH3:35][N:36](C=O)C>O>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([N:9]2[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([C:35]#[N:36])=[CH:3][CH:4]=3)[CH2:12][CH2:11][CH:10]2[C:13]2[CH:18]=[CH:17][C:16]([C:31]#[N:32])=[CH:15][CH:14]=2)=[CH:21][CH:22]=1)([CH3:28])([CH3:29])[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 582268372,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)pyrrolidineHCID 178418546HCID 178418546, compound

Product 1

HCID 672364944,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Example 42C (2.0 g, 3.9 mmol) and copper(I) cyanide (1.047 g, 11.69 mmol) in DMF (19 mL) was heated in a microwave for 7 hours at 160° C. Afterwards the mixture was poured in water (700 mL) and then concentrated ammonium hydroxide (40 mL) was added and the solution extracted with EtOAc. The organic extract was dried, filtered, concentrated and the residue purified by flash chromatography (silica gel, EtOAc/hexanes) to afford 1.23 g (78%) of the title compound. MS (ESI) m/z 406 (M+H)+.

Workup

  1. extractionthe solution extracted with EtOAc
  2. extractionThe organic extract
  3. customwas dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue purified by flash chromatography (silica gel, EtOAc/hexanes)

Sources & evidence

ORD record
ord-900f966cda17430b9a399a9099ce2e8c
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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