Thiophenol → 4-Acetamido-1-(6-phenylthio-2-pyridyl)piperidine

HRID 647511

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.ClC1C=CC=C(Cl)N=1.[Na].C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:37]([NH:40][C:41]1[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=1)(=[O:39])[CH3:38]>S1(CCCC1)(=O)=O>[C:37]([NH:40][CH:41]1[CH2:46][CH2:45][N:44]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)[CH2:43][CH2:42]1)(=[O:39])[CH3:38]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 9.5 g of 2-chloro-6-(phenylthio) pyridine (b.p. 112° to 116° C./0.01 mm Hg, prepared by reaction of 2,6-dichloropyridine with the sodium salt of thiophenol), 7.8 g of potassium carbonate and 7.6 g of 4-acetamidopyridine in 75 ml of sulfolane is heated to 150° C. with stirring for 50 hours, then the sulfolane is concentrated to 1/5th of its volume, the mixture is poured in 100 ml of water and extraction is effected four times with 150 ml of diethyl ether. The organic phase is washed with water, dried over anhydrous sodium sulfate, concentrated to dryness and the residue is crystallised in 40 ml of ethyl acetate. 6.8 g of 4-acetamido-1-(6-phenylthio-2-pyridyl)piperidine are thus obtained; m.p. 110° to 112° C.

Workup

concentrationthe sulfolane is concentrated to 1/5th of its volume
additionthe mixture is poured in 100 ml of water
extractionextraction
washThe organic phase is washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated to dryness
customthe residue is crystallised in 40 ml of ethyl acetate

Sources & evidence

ORD record: ord-617e70658e0147dbba88ec38debf31af
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04409228

Linked notes

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