Dimethylformamide → 3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	(3-Bromo-phenyl)-[(R)-1-(4-chloro-3-methyl-phenyl)-propyl]-amine	HCID 59393853	—
Reactant	HCID 178418306	HCID 178418306	—
Solvent	Diethyl Ether	HCID 3283	—
Product	3-[(R)-1-(4-Chloro-3-methyl-phenyl)-propylamino]-benzaldehyde	HCID 57517319	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To a solution of INT 6 (5.00 g, 14.8 mmol) in Et2O (148 mL) at −78° C. was added tBuLi (1.7 M in pentane, 34.7 mL, 59.0 mmol) dropwise. The mixture was stirred at −78° C. for 40 minutes and DMF (2.5 mL) was added. The reaction mixture was stirred at −78° C. for an additional 30 minutes. The mixture was quenched with saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/EtOAc) to afford INT 7.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08791100B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-0386c6d7cde2442bb521715b6bf87c8e
Source note	uspto-grants-2014_07