Methanesulfonyl chloride → HCID 22621928, compound

HRID 1066319Notes

Reaction equation

HRID 1066319 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([CH:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:25][OH:26])=[O:23])[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:33]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([CH:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:25][O:26][S:35]([CH3:34])(=[O:37])=[O:36])=[O:23])[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:33]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22621908HCID 22621908, compound

Product 1

HCID 22621928HCID 22621928, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 0.40 g (0.9 m mole) of 8-chloro-11-[1-(2-hydroxy-1-phenylethylcarbonyl)-4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta-[1,2-b]pyridine (Example 41 of Table 2) in 10 mL of pyridine and stir under nitrogen. Add 0.15 g (1.3 m mole) of methanesulfonyl chloride and stir for 20 hours. Concentrate under vacuo and triturate the residue with ether. Purify the resulting solid by silica gel chromatography using 2% MeOH saturated with amonia, and 98% CH2Cl2 as the solvent. The product is obtained as a white solid, mp=110.7-111.6° C.

Workup

  1. stirringstir for 20 hours
  2. concentrationConcentrate under vacuo
  3. customtriturate the residue with ether
  4. customPurify the resulting solid by silica gel chromatography
  5. customThe product is obtained as a white solid, mp=110.7-111.6° C.

Sources & evidence

ORD record
ord-09c372ecd80b438ab9fbfb9a915ce7ee
Source dataset
uspto-grants-2001_06
Patent number
US06242458B1

Reaction notes

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