Hydrogen Bromide → HCID 23047524, compound

HRID 1904302Notes

Reaction equation

[CH:1]([C:4](=[N:6][OH:7])[NH2:5])([CH3:3])[CH3:2].[O-]CC.[Na+].[CH3:12][N:13]1[CH2:18][C:17]([C:19]([O:21]C)=O)=[CH:16][CH2:15][CH2:14]1.Br.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>C(O)C>[C:24]([O-:29])(=[O:28])[C:25]([O-:27])=[O:26].[CH3:12][NH+:13]1[CH2:14][CH2:15][CH:16]=[C:17]([C:19]2[O:7][N:6]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[CH2:18]1.[CH3:12][NH+:13]1[CH2:14][CH2:15][CH:16]=[C:17]([C:19]2[O:21][N:6]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[CH2:18]1

Participants

Conditions

Temperature: 80 °C

Procedure

816 mg(8.0 mmol) of isopropylcarboxamide oxime was added to a solution of sodium ethoxide (7.8 mmol) in 20 ml of distilled ethanol and 5 g molecular sieves. The mixture was stirred at room temperature for 10 min whereafter 1.0 g(4.23 mmol) of arecoline, HBr was added. The mixture was heated at 80° C. for 12 hours, filtered, and evaporated in vacuo. 10 ml of water was added to the residue and the mixture was extracted with ether (3×50 ml). The combined extracts were dried with MgSO4 and evaporated in vacuo. The residue was dissolved in 5 ml of 99.9% ethanol and a solution of 380 mg(4.23 mmol) of oxalic acid in 10 ml of 99.9% ethanol was added. Crystallization from ether gave the title compound in 37% yield. M.P. 133°-134° C.

Workup

additionwas added
filtrationfiltered
customevaporated in vacuo
addition10 ml of water was added to the residue
extractionthe mixture was extracted with ether (3×50 ml)
dry with materialThe combined extracts were dried with MgSO4
customevaporated in vacuo
dissolutionThe residue was dissolved in 5 ml of 99.9% ethanol
customCrystallization from ether

Sources & evidence

ORD record: ord-d3edd0729743435880784b5410672d0d
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04837241

Reaction notes

Loading…