Thionyl Chloride → N-benzyl-2-chloro-N-methylethanamine

HRID 582626

Reaction equation

S(Cl)([Cl:3])=O.[CH2:5]([N:12]([CH2:14][CH2:15]O)[CH3:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:5]([N:12]([CH2:14][CH2:15][Cl:3])[CH3:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Thionyl chloride (2 ml) was added dropwise to a stirred, ice cooled solution of 2-[N-benzyl-N-methylamino]ethanol (4 g) obtained in preparation 8, in dry benzene (10 ml). The resulting mixture was stirred at 0° C. for 2 h and then diluted with ethyl acetate (40 ml), washed with saturated aqueous sodium bicarbonate solution (2×25 ml), water (50 ml), brine (50 ml) and dried. The ethyl acetate layer was evaporated and the residue was chromatographed on silica gel with 20% ethyl acetate in petroleum ether as eluent to give 2.6 g of the title compound.

Workup

washwashed with saturated aqueous sodium bicarbonate solution (2×25 ml), water (50 ml), brine (50 ml)
customdried
customThe ethyl acetate layer was evaporated
customthe residue was chromatographed on silica gel with 20% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record: ord-a1cbe317324b4b64b6db3f93ff4ac1d5
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925656

Linked notes

Loading…