Sodium Iodide → HCID 43267866, compound

HRID 1398015Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-hydroxy-5-methoxybenzaldehyde (0.761 g, 5 mmol), 1-(2-chloroethyl)piperidine hydrochloride (0.921 g, 5.00 mmol), K2CO3 (2.07 g, 14.99 mmol), and sodium iodide (0.075 g, 0.50 mmol) in acetonitrile (40 mL) was stirred at 100° C. overnight. The reaction was allowed to cool to ambient temperature and sat'd aqueous K2CO3 was added to the reaction mixture. The mixture was poured into a separatory funnel and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4, filtered through a bed of Celite, and conc. in vacuo to yield the product which was purified via silica gel chromatography (80 g) using EtOAc/hexanes (4:1) as eluent to yield the title compound as a brown oil (0.551 g, 42%); m/z 264.

Workup

temperatureto cool to ambient temperature
additionwas added to the reaction mixture
additionThe mixture was poured into a separatory funnel
extractionextracted with EtOAc
dry with materialThe organic phase was dried over anhydrous MgSO4
filtrationfiltered through a bed of Celite
customconc. in vacuo to yield the product which
customwas purified via silica gel chromatography (80 g)

Sources & evidence

ORD record: ord-946ce6dad726475a9a48e619d2567634
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901307B2

Reaction notes

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