Potassium Hydroxide → HCID 131714671, compound

HRID 2308992Notes

Reaction equation

HRID 2308992 reaction equation
[OH-].[K+].[OH:3][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>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.BrCCCBr.CCOCC>[NH2:9][CH2:8][CH2:7][CH2:6][O:3][C:4]12[CH:18]=[CH:17][CH:16]=[CH:15][CH:5]1[CH2:6][CH:7]2[CH2:8][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 131714666HCID 131714666, compound

Product 1

HCID 131714671HCID 131714671, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 3283Diethyl EtherSolventHCID 80011,3-DibromopropaneSolvent

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-ce094b21e8e84f04b71679bc4fd178db
Source dataset
uspto-grants-1987_09
Patent number
US04692445

Reaction notes

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