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

Participants

Role	Name	HCID	Charge
Reactant	Chloroform	HCID 6212	—
Reactant	Tetrafluoroboric acid	HCID 28118	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	2-(4-Bromophenyl)-1-methylpyrrolidine	HCID 284897	—
Reactant	Lithium Hexamethyldisilazide	HCID 2733832	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	4-(1-Methyl-2-pyrrolidinyl)benzenamine	HCID 59300155	—

Reaction Steps

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%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07713994B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-3f9ccca18cb041fd89fb8aabf9475d6d
Source note	uspto-grants-2010_05