Chloroacetyl chloride → HCID 21093752, compound

HRID 1349944Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N+:23]([O-])=O)[C:5]([OH:22])=[C:6]([CH:21]=1)[CH:7]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.C(=O)([O-])O.[Na+].Cl[CH2:32][C:33](Cl)=[O:34]>CO.[Pd].CC(=O)CC>[O:34]=[C:33]1[NH:23][C:4]2[CH:3]=[CH:2][CH:21]=[C:6]([CH2:7][CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[C:5]=2[O:22][CH2:32]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl 4-(5-bromo-2-hydroxy-3-nitrobenzylidene)piperidine-1-carboxylate (2.1 g, 4.9 mmol) in methanol (150 mL) was stirred under atmospheric hydrogen in the presence of 10% palladium on charcoal (0.5 g) for 4 h. The catalyst was removed by filtration and the filtrate was evaporated in vacuo to give a crude oil (1.8 g) which was taken up in 2-butanone (30 mL) and aqueous sodium hydrogen carbonate (1.3 g in water 20 mL). Chloroacetyl chloride (0.78 g) was added dropwise at 0° C. The mixture was stirred at 0° C. for further 2 h and then at 80° C. for 4 h. It was partitioned between water (50 mL) and ethyl acetate (100 mL). The organic layer was evaporated in vacuo. Silica gel chromatography of the resulting residue eluting with ethyl acetate in petroleum ether (20–30%) gave the title compound (1.5 g) as an oil.

Workup

customThe catalyst was removed by filtration
customthe filtrate was evaporated in vacuo
customto give a crude oil (1.8 g) which
waitat 80° C. for 4 h
customIt was partitioned between water (50 mL) and ethyl acetate (100 mL)
customThe organic layer was evaporated in vacuo
washSilica gel chromatography of the resulting residue eluting with ethyl acetate in petroleum ether (20–30%)

Sources & evidence

ORD record: ord-9dd5ff0851d44426bcac78de7978099c
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214674B2

Reaction notes

Loading…