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

HRID 280620Notes

Reaction equation

HRID 280620 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 steam 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 steam 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-db01ba0aa6b644429b9baeab7006caf3
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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