Piperidine → 7-Bromo-2-(3-pyridylmethylene)-1-tetralone

HRID 2413257Notes

Reaction equation

HRID 2413257 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1.N1CCCCC1>C(O)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[CH:19][C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 103713-PyridinecarboxaldehydeHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 539223587-Bromo-2-(3-pyridylmethylene)-1-tetraloneYield 81.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 7-bromo-1-tetralone (11.25 g), pyridin-3-carboxaldehyde (5.35 g), acetic acid (5 ml) and piperidine (6 ml) was heated on a stream bath for 6 hours and then allowed to stand for 18 hours. The volatile material was evaporated and the residue was dissolved in ethyl acetate. The solution was extracted several times with dilute hydrochloric acid and the combined extracts were made just alkaline with dilute sodium hydroxide solution. The solid was filtered off, washed with water and crystallised from methanol to give 7-bromo-2-(3-pyridylmethylene)-1-tetralone (12.8 g), m.p. 124°-125°.

Workup

  1. temperaturewas heated on a stream bath for 6 hours
  2. customThe volatile material was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. extractionThe solution was extracted several times with dilute hydrochloric acid
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customcrystallised from methanol

Sources & evidence

ORD record
ord-46dea84cae274694b8b3834e7a6b459f
Source dataset
uspto-grants-1985_01
Patent number
US04496572

Reaction notes

Loading…