Water → HCID 21435163, compound

HRID 2398293Notes

Reaction equation

HRID 2398293 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:17]3[CH:16]=[CH:15][S:14][C:13]=3[C:12](=[O:18])[CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)[CH2:4][CH2:3]1.[CH3:23]C([O-])(C)C.[K+].CI.O>C1CCCCC1.C1C=CC=CC=1>[CH3:23][CH:11]1[C:12](=[O:18])[C:13]2[S:14][CH:15]=[CH:16][C:17]=2[C:8](=[C:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[C:9]2[CH:22]=[CH:21][CH:20]=[CH:19][C:10]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 3827KetotifenHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxide

Product 1

HCID 21435163HCID 21435163, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8078CyclohexaneSolvent

Procedure

24.5 g of 4-(1-methyl-4-piperidylidene)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-10(9H)-one were dissolved in 750 ml of boiling cyclohexane. The mixture was cooled to 50° and whilst this temperature was maintained 10.7 g of potassium tert-butylate were added. The resulting suspension was cooled to 20°, and whilst this temperature was maintained 12.4 g of methyl iodide were slowly added dropwise. The mixture was stirred for a further 1 hour and then treated with 100 ml of water and 100 ml of benzene. The organic phase was separated off and evaporated to yield crude 9-methyl-4-(1-methyl-4-piperidylidene)-4H-benzo[4,5]cyclohepta[1,2-b]thiophene-10(9H)-one as an oil which can be used further in crude form (M.Pt. of hydrogen fumarate 213°-215° from ethanol).

Workup

  1. temperatureThe mixture was cooled to 50° and whilst this temperature
  2. additionwere added
  3. temperatureThe resulting suspension was cooled to 20°
  4. additionwere slowly added dropwise
  5. customThe organic phase was separated off
  6. customevaporated

Sources & evidence

ORD record
ord-ce96cd164a034d768c6786b2efae7b3a
Source dataset
uspto-grants-1977_05
Patent number
US04024266

Reaction notes

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