heptabarb Chemical Properties

Melting point:

174°

Boiling point:

393.43°C (rough estimate)

Density 

1.1307 (rough estimate)

refractive index 

1.6450 (estimate)

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml; Ethanol: 10 mg/ml

form 

A crystalline solid

pka

7.77±0.10(Predicted)

Water Solubility 

250.3mg/L(25 ºC)

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

heptabarb Usage And Synthesis

Chemical Properties

White, crystalline powder; odorless; slightly bitter taste.Very sparingly soluble in water; slightly soluble in alcohol; soluble in alkaline solutions. Forms water-soluble sodium, magnesium, and calcium salts.

Originator

Medomine,Ciba Geigy,France,1948

Uses

Medicine (sedative).

Definition

ChEBI: Heptabarbital is a member of barbiturates.

Manufacturing Process

112 g of cycloheptanone (suberone) are mixed with 130 g of cyanoacetic acid methyl ester, 2 g of piperidine are added, and the mixture is heated on the water bath at 60°C for several hours until no more water separates from the reaction mixture. The water layer is removed, and the remainder is subjected to distillation in vacuo. The fraction distilling at 160°C to 175°C under a pressure of 20 mm is collected separately; it consists of cycloheptenylcyanoacetic acid methyl ester. The first fractions can be subjected to a fresh condensing reaction after addition of more piperidine.
The cycloheptenyl-cyanoacetic acid methyl ester so obtained is a colorless liquid boiling at 174°C under a pressure of 20 mm.
Into this compound, an ethyl radical is introduced at the same C-atom to which the cycloheptenyl radical is connected. This is done, for example, in the following way:
19.3 g of the above ester are added to a solution of 2.3 g of sodium in 40 cc of absolute ethyl alcohol. To this mixture, 13.0 g of ethyl bromide are gradually added while cooling, and the reaction mixture is heated under reflux on a water bath until it has become neutral. The mixture is then taken up in water, the aqueous layer is separated and the cycloheptenyl-ethyl-cyanoacetic acid methyl ester so formed distills at 169°C to 170°C under a pressure of 20 mm.
22.1 g of this latter substance are dissolved in a solution of 4.6 g of sodium in 100 cc of absolute ethyl alcohol. 12 g of urea are further added thereto, and the whole solution is heated to about 80°C for about eight hours. The alcohol is then distilled off in vacuo, the residue is dissolved in cold water, and from this solution, C-C-cycloheptenyl-ethyl barbituric acid is obtained by saponification with diluted hydrochloric acid. The crude product is recrystallized from diluted ethyl alcohol and forms colorless needles of faintly bitter taste and melting point 174°C.
The sodium salt of this acid may be prepared by dissolving 2.5 g of the acid in a solution of 0.23 g of sodium in 20 cc of ethyl alcohol, and the salt forms, after evaporating the alcohol, a colorless, water-soluble powder.

brand name

Medapan;Medomina.

Therapeutic Function

Hypnotic, Sedative

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