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

HRID 1471019Notes

Reaction equation

HRID 1471019 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.[C:30]([Cu])#[N:31].[CH3:33][NH:34]C.O>CN(C)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:33]#[N:34])=[CH:3][CH:4]=3)[CH2:12][CH2:11][CH:10]2[C:13]2[CH:18]=[CH:17][C:16]([C:30]#[N:31])=[CH:15][CH:14]=2)=[CH:21][CH:22]=1)([CH3:28])([CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 27521Dimethylamine, hydrateHCID 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 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 42C (1.0 g, 1.948 mmol) and CuCN (523 mg, 5.84 mmol) in Dimethylformamide (9.5 mL) was heated to 160° C. for 4.5 hours in a microwave. Mixture was poured into a dimethylamine/H2O mixture (1/10) and extracted with EtOAc (3×150 mL). The combined organics were washed with H2O and Brine. The organic was then dried (MgSO4), filtered and concentrated. Purification by chromatography (silica gel, 20% EtOAc in Hexanes) afforded 395 mg (50%) of the title compound. MS (ESI) m/z 406 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×150 mL)
  2. washThe combined organics were washed with H2O and Brine
  3. dry with materialThe organic was then dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica gel, 20% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-1d725e0fbfe2452a83438b2a09d39b18
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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