Sodium Hydroxide → HCID 19747237, compound

HRID 484309Notes

Reaction equation

S(Cl)(Cl)=O.[CH3:5][S:6][C:7]1[CH:8]=[CH:9][C:10]2[C:20]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)(O)[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH2:13][CH2:12][C:11]=2[CH:29]=1.[OH-].[Na+]>>[CH3:5][S:6][C:7]1[CH:8]=[CH:9][C:10]2[C:20](=[C:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH2:13][CH2:12][C:11]=2[CH:29]=1

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 24386Thionyl Chloride

HCID 19747288HCID 19747288, compound

Product 1

HCID 19747237HCID 19747237, compoundYield 61.4%

Procedure

Thionyl chloride (6 ml) was added to 1.03 g of 8-methylthio-6,11-dihydro-11-(1-methyl-4-piperidyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol and the resulting mixture was refluxed for 1 hour. After the completion of the reaction, the reaction mixture was added with a 10% sodium hydroxide solution and then extracted with chloroform. The resultant extract was dried over anhydrous Na2SO4 and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column and, from relevant fractions eluted with chloroform:methanol (20:1), 0.6 g of 8-methylthio-11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine was obtained (yield: 61%).

Workup

temperaturethe resulting mixture was refluxed for 1 hour
customAfter the completion of the reaction
extractionextracted with chloroform
extractionThe resultant extract
dry with materialwas dried over anhydrous Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customThe residue was purified by chromatography on a silica gel column and, from relevant fractions
washeluted with chloroform:methanol (20:1)

Sources & evidence

ORD record: ord-f47eea16674d4573b0ba1a01ff75386d
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05231101

Reaction notes

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