1-Azabicyclo[2.2.2]octane-4-carbonitrile → 1-Azabicyclo[2.2.2]octane-4-carbonitrile, 4-methylbenzenesulfonate (1:1)

HRID 2414124Notes

Reaction equation

[C:1]([C:3]12[CH2:10][CH2:9][N:6]([CH2:7][CH2:8]1)[CH2:5][CH2:4]2)#[N:2].O.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(O)C>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[C:1]([C:3]12[CH2:10][CH2:9][N:6]([CH2:7][CH2:8]1)[CH2:5][CH2:4]2)#[N:2]

Participants

Conditions

Temperature: 40 °C

Procedure

4-Cyanoquinuclidine (85.0 g) was suspended in ethanol (200 ml), followed by an addition of a solution of p-toluenesulfonic acid monohydrate (119 g) in ethanol (350 ml). The resulting mixture was then stirred at 40° C. for 1 hour. The reaction mixture was cooled with ice and the precipitated crystals were collected by filtration. They were then washed with ethanol and diethylether to obtain 182.9 g of 4-cyanoquinuclidine p-toluenesulfonate as colorless crystals (yield: 95%).

Workup

temperatureThe reaction mixture was cooled with ice
filtrationthe precipitated crystals were collected by filtration
washThey were then washed with ethanol and diethylether

Sources & evidence

ORD record: ord-b670a38c615b4a8e9f9c432cb1a3a616
Source dataset: uspto-grants-1988_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04721788

Reaction notes

Loading…