PREPARATION OF PIPERIDYL-STEROIDS

• US 3,673,175 A
• Filed: 04/26/1971
• Issued: 06/27/1972
• Est. Priority Date: 04/24/1970
• Status: Expired due to Term

• Current Assignee: Geza Schramm, Horst Riedl
• Original Assignee: Geza Schramm, Horst Riedl
• Inventors: Schramm, Geza, Riedl, Horst
• Primary Examiner(s): Roberts, Elbert L.
• Application Number:
  US05/137,699
• Time in Patent Office: 428 Days
• Field of Search: 260/239.5
• US Class Current: 540/109
• CPC Class Codes: C07J 43/003 not condensed

Abstract

The preparation of piperidyl-steroids having an oxygencontaining group in the 16-position which comprises reacting C16bromo-cyanamides, in a predominantly aprotic and polar medium with an alkali metal salt of a lower aliphatic carboxylic acid or of benzoic acid, isolating the resulting 16-acyloxy-cyanamide and then reducing this compound to remove the nitrile group.

Claims

2. A process according to claim 1, in which the reaction with the alkali metal salt is carried out in a solvent selected from the group consisting of dimethylformamide, dimethylsulphoxide, acetonitrile and hexamethylphosphoric acid tris-amide.

3. A process according to claim 1, in which the alkali metal salt is employed as a concentrated aqueous solution thereof.

4. A process according to claim 1, in which the reaction with the alkali metal salt is carried out at a temperature within the range of 80* to 150* C.

5. A process according to claim 1, in which the alkali metal salt is selected from the group consisting of potassium acetate and sodium acetate.

6. A process according to claim 1, in which the 16-acyloxy-cyanamide derivative of Formula III is precipitated by pouring the reaction mixture from the reaction with the alkali metal salt into water and is isolated in the solid form.

7. A process according to claim 1, in which a compound selected from the group consisting of lithium aluminum hydride, sodium aluminium hydride and sodium dihydro-bis-methoxyethoxyalanate is used for the reduction of the 16-acyloxy compound of the Formula III.