Triethylamine → HCID 131717424, compound

HRID 892741Notes

Reaction equation

[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Cl:9])[CH:3]=1.Cl.[C:11]1([C:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][SH:25])[CH2:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>CN(C)C=O>[ClH:9].[ClH:1].[C:11]1([C:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][S:25][CH2:8][C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)[CH2:19][CH:18]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3-picolyl chloride hydrochloride (2.50 g) and 3,6-dihydro-4-phenyl-1(2H)-pyridineethanethiol hydrochloride (3.90 g) (Example A) in 100 mL of dimethylformamide is treated with triethylamine (7.4 ml) and the mixture is heated at 80° C. for 8 hours. The solvent is evaporated in vacuo, and the residue is partitioned into chloroform/sodium bicarbonate solution. The organic extract is dried over magnesium sulfate, filtered and concentrated. The crude product is purified by column chromatography (silica gel; 2% methanol in chloroform) to yield 1.7 g of the title compound as an oil, which is converted into its hydrochloride salt (hydrogen chloride gas in diethyl ether) and recrystallized from ethanol/acetonitrile; mp 218°-220° C. (dec).

Workup

customThe solvent is evaporated in vacuo
customthe residue is partitioned into chloroform/sodium bicarbonate solution
extractionThe organic extract
dry with materialis dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product is purified by column chromatography (silica gel; 2% methanol in chloroform)

Sources & evidence

ORD record: ord-5583e05ea6a149208541f556327f8141
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05120748

Reaction notes

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