Water → 1-(4-Tert-butylphenyl)-2,5-bis(4-chloro-3-nitrophenyl)pyrrolidine

HRID 1470925Notes

Reaction equation

HRID 1470925 reaction equation
CS(O[CH:6]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([N+:32]([O-:34])=[O:33])[CH:26]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1)(=O)=O.[C:35]([C:39]1[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=1)([CH3:38])([CH3:37])[CH3:36].O>CN(C=O)C>[C:35]([C:39]1[CH:40]=[CH:41][C:42]([N:43]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=3)[CH2:8][CH2:7][CH:6]2[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([N+:32]([O-:34])=[O:33])[CH:26]=2)=[CH:44][CH:45]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 962WaterHCID 698614-Tert-ButylanilineHCID 767087941,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 582268181-(4-Tert-butylphenyl)-2,5-bis(4-chloro-3-nitrophenyl)pyrrolidineYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

The product from Example 28C (6.6 g, 11.84 mmol) was slurried in DMF (30 mL) and 4-t-butyl aniline (18.7 mL, 118 mmol) was added and the solution was heated at 55° C. for 2 h then cooled and poured into water and extracted into dichloromethane. The organics were concentrated and the residue was purified by chromatography on silica gel 120 g column, eluting with 0-5% ethyl acetate/hexanes to give 4.41 g (72%) of a thick oil.

Workup

  1. temperaturethen cooled
  2. extractionextracted into dichloromethane
  3. concentrationThe organics were concentrated
  4. customthe residue was purified by chromatography on silica gel 120 g column
  5. washeluting with 0-5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9e2f7335842e46fca8255e74d8705d40
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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