1,3-Dibromopropane → HCID 20137129, compound

HRID 280155Notes

Reaction equation

HRID 280155 reaction equation
[OH-].[K+].O[C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Br:19][CH2:20][CH2:21][CH2:22]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:19][CH2:20][CH2:21][CH2:22][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 13711140HCID 13711140, compound

Product 1

HCID 20137129HCID 20137129, compound

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

Potassium hydroxide (53 g, 87%) is added over a period of 1 hour 15 min to a stirred suspension of 4-hydroxy-1-piperidinylindan (30 g), and tetrabutylammonium chloride (4.1 g) in 1,3-dibromopropane (140 ml) and the resulting mixture stirred at RT under nitrogen for two hours. The reaction mixture is partitioned between ice-water and ether and the aqueous layer separated and extracted with ether. The combined organic extracts are washed with water and ice cold 5% aqueous HCl forming a precipitate which is filtered and washed with ether. The acidic fraction is made strongly alkaline forming an oil precipitate which is extracted into ether. The combined ether layers are washed, dried over Na2SO4, filtered and concentrated in vacuo yielding the desired product as an oil which is used in the next step without further treatment.

Workup

  1. customThe reaction mixture is partitioned between ice-water and ether
  2. customthe aqueous layer separated
  3. extractionextracted with ether
  4. washThe combined organic extracts are washed with water and ice cold 5% aqueous HCl forming a precipitate which
  5. filtrationis filtered
  6. washwashed with ether
  7. customforming an oil precipitate which
  8. extractionis extracted into ether
  9. washThe combined ether layers are washed
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55af7c317fc44146994bf071eebe0327
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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