HCID 54449443, compound → 8-Chloro-11-(1-methylpiperidin-4-ylidene)-11H-benzo[5,6]cyclohepta[1,2-b]pyridine

HRID 1534581Notes

Reaction equation

HRID 1534581 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]([CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)(O)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=[CH:7][C:6]=2[CH:24]=1>S(=O)(=O)(O)O.FC(F)(F)S(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=[CH:7][C:6]=2[CH:24]=1

Participants

4

Reactant 1

HCID 54449443HCID 54449443, compound

Product 1

HCID 229147868-Chloro-11-(1-methylpiperidin-4-ylidene)-11H-benzo[5,6]cyclohepta[1,2-b]pyridineYield 94.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 847 mg (2.48 mmole) of 8-chloro-11-(1-methyl-4-piperidinyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol in 5 mL of concentrated sulfuric acid and 5 mL of trifluoromethane sulfonic acid was heated at 70° C. for 4 hr 10 min. The mixture was cooled to room temperature, poured into ice cold 30% aqueous KOH, and extracted three times with CH2Cl2The organic portions were combined, washed once with water, dried over MgSO4, filtered, and concentrated in vacuo to yield 755 mg (94%) of the title compound as a glass.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted three times with CH2Cl2The organic portions
  3. washwashed once with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8788df2e90ad4ee5a2b19081367b5dfd
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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