Thiophenol → 4-Acetamido-1-(6-phenylthio-2-pyridyl)piperidine
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
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
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
- Patent number
- US04409228
Reaction notes
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