Methanesulfonyl chloride → HCID 22621928, compound

HRID 861735Notes

Reaction equation

HRID 861735 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 ammonia, and 98% CH2 Cl2 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-bf547f5a5a98461b99b9a5dbc8649bbd
Source dataset
uspto-grants-1998_02
Patent number
US05714609

Reaction notes

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