1,3-Dibromopropane → HCID 13799026, compound

HRID 280165Notes

Reaction equation

HRID 280165 reaction equation
[OH-:1].[K+].O[C:4]12[CH:18]=[CH:17][CH:16]=[CH:15][CH:5]1[CH2:6][CH:7]2[CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Br:19][CH2:20][CH2:21][CH2:22]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>[Br:19][CH2:20][CH2:21][CH2:22][O:1][C:17]1[CH:18]=[C:4]2[CH:7]([CH2:8][N:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[CH2:6][C:5]2=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 131714666HCID 131714666, compound

Product 1

HCID 13799026HCID 13799026, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Potassium hydroxide (1.5 g, 10%) is added over a period of 1 hour 15 min to a stirred suspension of 3-hydroxy-1-(1-piperidinylmethyl)benzocyclobutene (1.0 g), and tetrabutylammonium chloride (0.13 g) in 1,3-dibromopropane (4.6 ml) and the resulting mixture stirred at RT under nitrogen for two days. The reaction mixture is partitioned between ice-water and ether and the aqueous layer separated and extracted with ether. The combined organic extract is washed with water, ice cold 5% aqueous HCl thereby forming a precipitate which is filtered and washed with ether. The acidic layer is alkalized forming an oily precipitate which is taken up in ether. The combined ether fractions are washed with water, dried over Na2SO4, filtered and concentrated in vacuo yielding the desired product as an oil which is used in the next step without further purification.

Workup

  1. customThe reaction mixture is partitioned between ice-water and ether
  2. customthe aqueous layer separated
  3. extractionextracted with ether
  4. extractionThe combined organic extract
  5. washis washed with water, ice cold 5% aqueous HCl
  6. customthereby forming a precipitate which
  7. filtrationis filtered
  8. washwashed with ether
  9. customThe acidic layer is alkalized forming an oily precipitate which
  10. washThe combined ether fractions are washed with water
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99959137c08b437cbbd1653b542580bd
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

Loading…