Hydrochloric Acid → 4-(9,10-dihydro-10-methyl-4H-benzo[4,5]-cyclohepta[1,2-b]thiophen-4-ylidene)-1-methylpiperidine

HRID 27694Notes

Reaction equation

HRID 27694 reaction equation
[CH3:1][CH:2]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6]([CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)(O)[C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[CH2:3]1.Cl>C(O)(C)C>[CH3:1][CH:2]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C:6](=[C:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]2)[C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 233418319,10-dihydro-10-methyl-4-(1-methyl-4-piperidyl)-4H-benzo[4,5]cyclohepta-[1,2-b]thiophen-4-ol

Product 1

HCID 1915134-(9,10-dihydro-10-methyl-4H-benzo[4,5]-cyclohepta[1,2-b]thiophen-4-ylidene)-1-methylpiperidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 17.0 g of 9,10-dihydro-10-methyl-4-(1-methyl-4-piperidyl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol in 350 cc of isopropanol and 350 cc of a 7 N solution of hydrogen chloride in isopropanol is heated to the boil for 4 hours, is evaporated to dryness, the residue is taken up in 150 cc of water, is made alkaline with concentrated caustic soda solution and extracted with methylene chloride. The extracts are washed with water, dried over potassium carbonate, decolourized with animal charcoal and concentrated by evaporation. The title compound, obtained as oily residue, is converted into the hydrochloride form in ethanol. M.P. of the hydrochloride form of the title compound: decomp. from 210° (from acetone/ethanol). M.P. (hydrogen malonate 191°-2° C.)

Workup

  1. customis evaporated to dryness
  2. extractionextracted with methylene chloride
  3. washThe extracts are washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fd5b0b9afed143d097860fd4bae4fff1
Source dataset
uspto-grants-1980_09
Patent number
US04223035

Reaction notes

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