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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	4-Tert-Butylaniline	HCID 69861	—
Reactant	1,4-Bis(4-chloro-3-nitrophenyl)butane-1,4-diyl dimethanesulfonate	HCID 76708794	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-(4-Tert-butylphenyl)-2,5-bis(4-chloro-3-nitrophenyl)pyrrolidine	HCID 58226818	72.4%

Reaction Conditions

Temperature	55 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09006387B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-9e2f7335842e46fca8255e74d8705d40
Source note	uspto-grants-2015_04