Tetrahydrofuran → HCID 19747266, compound

HRID 484310Notes

Reaction equation

HRID 484310 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:18](=[O:19])[C:13]3[NH:14][CH2:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:20]=1)(=[O:4])=[O:3].[CH3:21][N:22]1[CH2:27][CH2:26][CH:25](Cl)[CH2:24][CH2:23]1.[Mg].C1COCC1>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:18]([CH:25]3[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]3)([OH:19])[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11][CH2:10][C:9]=2[CH:20]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 19747285HCID 19747285, compound

Product 1

HCID 19747266HCID 19747266, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Methylsulfonyl-5,6-dihydro-1H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (1 g) was dissolved in 30 ml of methylene chloride, followed by the dropwise gradual addition of a Grignard reagent under ice cooling. The Grignard reagent had been prepared from 0.07 g of N-methyl-4-chloropiperidine, 0.012 g of magnesium and 10 ml of THF. After the resultant mixture was stirred for 1 hour at the same temperature, it was stirred for additional 1 hour at room temperature. The reaction mixture was then treated in a similar manner to Referential Example 2, whereby 0.82 g of the target compound, 8-methylsulfonyl-6,11-dihydro-11-(1-methyl-4-piperidyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol was obtained (yield: 61%).

Sources & evidence

ORD record
ord-150c0e4170244b71b0fe4ac95968220f
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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