HCID 22621928, compound → HCID 22621924, compound

HRID 840269Notes

Reaction equation

HRID 840269 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:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:25]OS(C)(=O)=O)=[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:37]=1.[C:38]([O-:41])(=[S:40])[CH3:39].[Cs+]>CN(C=O)C>[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:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:25][S:40][C:38](=[O:41])[CH3:39])=[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:37]=1

Participants

4

Reactant 2

HCID 22621928HCID 22621928, compound2×HCID 23720634HCID 23720634, compound

Product 1

HCID 22621924HCID 22621924, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 0.3 g (0.56 m mole) of 8-chloro-11-[1-(2-methanesulfonyloxy-1-phenylethylcarbonyl)-4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta-[1,2-b]pyridine (Formula 5.6 of Example 83) in 5 mL of DMF and add 0.2 g (0.6 m mole) of cesium thioacetate (preparation described in Synthetic Communications, 13, 553, 1983). Stir the reaction at 80° C. for twenty hours then concentrate under vacuo. Purify the residue by silica gel chromatography using 70% EtOAc and 30% hexane as the solvent. The product is obtained as a light brown solid, mp=92.7-93° C.

Workup

  1. customthe reaction at 80° C. for twenty hours
  2. concentrationthen concentrate under vacuo
  3. customPurify the residue by silica gel chromatography
  4. customThe product is obtained as a light brown solid, mp=92.7-93° C.

Sources & evidence

ORD record
ord-65513693b9c94661b7f48b9a673bd4ab
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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