Chloroform → 4-(1-Methyl-2-pyrrolidinyl)benzenamine

HRID 2236496Notes

Reaction equation

HRID 2236496 reaction equation
[Li+].C[Si]([N-:6][Si](C)(C)C)(C)C.C(Cl)(Cl)Cl.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F.Br[C:35]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:45][CH2:44][CH2:43][N:42]2[CH3:46])=[CH:37][CH:36]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:46][N:42]1[CH2:43][CH2:44][CH2:45][CH:41]1[C:38]1[CH:39]=[CH:40][C:35]([NH2:6])=[CH:36][CH:37]=1

Participants

8

Reactant 5

HCID 6212ChloroformHCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2848972-(4-Bromophenyl)-1-methylpyrrolidineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 593001554-(1-Methyl-2-pyrrolidinyl)benzenamine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

LiHMDS (5.0 g, 30.0 mmol) is added to a 250 mL round bottom flask. Toluene (60 mL) is then added followed by addition of Pd2(dba)3.CHCl3 (390 mg, 0.39 mmol) and P(tBu)3.HBF4 (300 mg, 1.03 mmol) and 2-(4-Bromo-phenyl)-1-methyl-pyrrolidine (3.5 g, 14.5 mmol). The mixture is degassed. The resulting mixture is then stirred at room temperature overnight. After TLC suggested no starting bromide left, the reaction mixture is diluted with ether and poured into dilute HCl (aq). The ether layer is discarded, the aqueous layer is basified with NH4OH and extracted with CH2Cl2. The CH2Cl2 layer is dried and concentrated. The residue is judged by NMR to be 90% purity product (2.52 g, 90%).

Workup

  1. customThe mixture is degassed
  2. waitleft
  3. additionthe reaction mixture is diluted with ether
  4. additionpoured into dilute HCl (aq)
  5. extractionextracted with CH2Cl2
  6. dry with materialThe CH2Cl2 layer is dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3f9ccca18cb041fd89fb8aabf9475d6d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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