Potassium Hydroxide → HCID 12909376, compound

HRID 1248161Notes

Reaction equation

HRID 1248161 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:19]([O:21]CC)=[O:20])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)[CH2:4][CH2:3]1.[OH-].[K+]>CO>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12909378HCID 12909378, compound

Product 1

HCID 12909376HCID 12909376, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.24 g of (-)-ethyl 5-(1-methyl-4-piperidylidene)-5H-dibenzo[a,d]cycloheptene-3-carboxylate and 4.12 ml of 2N potassium hydroxide in 55 ml of methanol was stirred at room temperature for seven days. The methanol was removed by evaporation at 25°. The residue was dissolved in water and extracted with 50 ml of ether. The clear, colorless aqueous phase was acidified with glacial acetic acid. The white precipitate that formed was removed by filtration, and washed thoroughly with water. After drying at 100° in vacuo, 1.08 g of (-)-5-(1-methyl-4-piperidylidene)-5H-dibenzo[a,d]cycloheptene-3-carboxylic acid was obtained, m.p. 300°-305°; [α]58925 -180°; [α]57825 -194°; [α]54625 -239°; [α]43625 -675°; (c=0.004968 g/ml 0.10 NHCl). Rf : 0.70 (fluorescent silica gel, n-butanol/acetic acid/water (5:2:3).

Workup

  1. customThe methanol was removed by evaporation at 25°
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with 50 ml of ether
  4. customThe white precipitate that formed
  5. customwas removed by filtration
  6. washwashed thoroughly with water
  7. customAfter drying at 100° in vacuo

Sources & evidence

ORD record
ord-d92577c5ccc44e74af82b9f826fb5dfc
Source dataset
uspto-grants-1985_06
Patent number
US04522821

Reaction notes

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