Process for the synthesis of an annulated pyridine base

• US 6,495,690 B2
• Filed: 03/27/2001
• Issued: 12/17/2002
• Est. Priority Date: 03/27/2001
• Status: Expired due to Fees

• Current Assignee: Council of Scientific & Industrial Research
• Original Assignee: Council of Scientific & Industrial Research
• Inventors: Raghavan, Kondapuram Vijaya, Kulkarni, Shivanand Janardan, Vippagunta, Radha Rani, Nagabandi, Srinivas
• Primary Examiner(s): DENTZ, BERNARD I
• Application Number:
  US09/818,281
• Publication Number:
  US 20020173651A1
• Time in Patent Office: 630 Days
• Field of Search: 546/102, 546/93, 546/79
• US Class Current: 546/102
• CPC Class Codes: C07D 219/02 with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 221/16 containing carbocyclic rings other than six-membered

Abstract

This invention relates to process for producing annulated pyridine bases by reacting cyclic ketones with aliphatic aldehyde in presence of ammonia in gaseous phase in the presence of a catalyst. This process provides an eco-friendly, more economical and highly selective heterogeneous method.

Claims

1. A process for the synthesis of an annulated pyridine base, wherein said annulated pyridine base is selected from,

said process comprising reacting a cyclic ketone containing 5 to 8 carbon atoms and an aliphatic aldehyde having the formula R₁CHO, wherein R₁ is hydrogen or alkyl having 1 to 3 carbon atoms, with ammonia in a gaseous phase in the presence of a mesoporous sieve catalyst to obtain said annulated pyridine base, wherein the mole ratio of ammonia to cyclic ketone is in the range of 0.5 to 5.0 and the reaction temperature is in the range of 350°

C. to 450°

C.

2. A process as claimed in claim 1, wherein the cyclic ketone is cyclohexanone and the aliphatic aldehyde is formaldehyde to obtain 1,2,3,4,5,6,7,8-octahydro acridine.

3. A process as claimed in claim 2, wherein the cyclohexanone, formaldehyde and ammonia have a molar ratio of 1:

1;

0.5-5.

4. A process as claimed in claim 3, wherein methanol is added in an amount up to 0.5 mole per mole of cyclohexanone.

5. A process as claimed in claim 1, wherein the temperature of the reaction is in the range of 300 to 400°

C.

6. A process as claimed in claim 1, wherein the aliphatic aldehyde is acetaldehyde to obtain 9-methyl octahydro acridine.

7. A process as claimed in claim 1, wherein the aliphatic aldehyde is propionaldehyde to obtain 9-ethyl octaohydro acridine.

8. A process as claimed in claim 1, wherein the aliphatic aldehyde is butyraldehyde to obtain 9-propyl octahydro acridine.

9. A process as claimed in claim 1, wherein the cyclic ketone is cyclopentanone to obtain bis cyclo pentyl pyridine.

10. A process as claimed in claim 1, wherein the cyclic ketone is cyclooctanone to obtain bis cyclooctyl pyridine.

11. A process as claimed in claim 1, wherein the mesoporous sieve catalyst comprises Si and Al in a proportion of 2.5 to 25.

12. A process as claimed in claim 1 wherein the mesoporous sieve catalyst is selected from the group consisting of Al-MCM-41, ZSM-5, HY and H-BEA and mixtures thereof.