Acetone Cyanohydrin → HCID 45277266, compound

HRID 1942442Notes

Reaction equation

CS([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)(=O)=O.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.CC(C)(O)[C:24]#[N:25].C(N(CC)CC)C>CO>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:19]2[CH:8]3[CH2:9][CH2:10][C:5]2([C:24]#[N:25])[CH2:6][CH2:7]3)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

This synthesis was performed according to scheme 2, with details as follows. In a dry, pressure resistant vessel of 20 ml, 1.25 g (6.5 mmole) 4-methanesulfonylcyclohexanone 9, 0.89 g (6.5 mmole) 4-methoxybenzylamine, 1.11 g (13 mmole) acetone cyanohydrine and 1.32 g (13 mmole) triethylamine were dissolved in 16 ml dry methanol. The vessel was closed and heated to 100° C. for 50 hours. Methanol was evaporated and the residue was redissolved in dichloromethane. The solution was washed with a saturated NaHCO3 solution and dried over MgSO4. After filtration of the solids, the volatile components were evaporated. 7-(4-methoxybenzyl)-7-azabicyclo[2.2.1]heptane-1-carbonitrile 6a was obtained as a brown oil in a 97% yield and characterised by proton (1H-NMR) and carbon (13C-NMR) nuclear magnetic resonance, and mass spectrum (MSES) as follows:

Workup

customThe vessel was closed
customMethanol was evaporated
dissolutionthe residue was redissolved in dichloromethane
washThe solution was washed with a saturated NaHCO3 solution
dry with materialdried over MgSO4
filtrationAfter filtration of the solids
customthe volatile components were evaporated

Sources & evidence

ORD record: ord-69fbcc40a3db4270b4c7f3028bc811db
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389561B2

Reaction notes

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