Formaldehyde → HCID 86646690, compound

HRID 1510024Notes

Reaction equation

[CH3:1][C:2]12[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:3]1[NH:4][CH2:5][CH2:6][CH2:7]2.C=O.[C:17](=O)([O-])O.[Na+].[CH3:22][S:23]([O-:26])(=[O:25])=[O:24].CS(O)(=O)=O>O1CCCC1.C(O)=O>[CH3:22][S:23]([OH:26])(=[O:25])=[O:24].[CH3:17][N:4]1[CH2:5][CH2:6][CH2:7][C:2]2([CH3:1])[CH2:14][C:13]3[C:8]([CH:3]12)=[CH:9][CH:10]=[CH:11][CH:12]=3

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (4aRS,9bRS)-4a-methyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridine (140 mg) in tetrahydrofuran (3 ml) were added a 35% formalin solution (0.55 ml) and formic acid (0.3 ml), and the mixture was stirred at 80° C. for 1 hour. An excessive amount of a saturated aqueous sodium hydrogen carbonate solution was added thereto for neutralization, followed by extraction with chloroform, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain an oily substance (150 mg). This was made into a methanesulfonate using an equivalent amount of methanesulfonic acid by a conventional method, washed with ethyl acetate, and collected by filtration to obtain (4aRS,9bRS)-1,4a-dimethyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridine methanesulfonate (193 mg) as a colorless powder.

Workup

extractionfor neutralization, followed by extraction with chloroform
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customto obtain an oily substance (150 mg)
washwashed with ethyl acetate
filtrationcollected by filtration

Sources & evidence

ORD record: ord-3456d22dc2f94b049eabc2ed64e082db
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211907B2

Reaction notes

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