Hydrochloric Acid → HCID 23045641, compound

HRID 2413788Notes

Reaction equation

HRID 2413788 reaction equation
[ClH:1].[CH2:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH2:6]1)[CH2:3][CH3:4].[CH2:18](Br)[CH:19]=[CH2:20].[OH-].[Na+].Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[ClH:1].[CH2:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:20][CH:19]=[CH2:18])[CH:12]=2)[CH2:6]1)[CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 1574713-(1-Propylpiperidin-3-yl)phenol--hydrogen chloride (1/1)

Product 1

HCID 23045641HCID 23045641, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

(-)N-n-propyl-3-(3-hydroxyphenyl)piperidine hydrochloride (0.255 g, 1 mmol) and tetrabutylammonium hydrogen sulphate (0.340 g, 1 mmol) were suspended in dichloromethane (2 ml) and allylbromide (0.133 g, 1.1 mmol). 2-M NaOH (2 ml) was added during two minutes and the mixture was stirred at room temperature for half an hour. The layers were separated and the organic layer was dried over Na2SO4. After removal of the solvent by distillation, the residual oil was dissolved in ether (50 ml). A theoretical quantity of tetrabutylammonium iodide was precipitated. The precipitate was filtered off and to the filtrate was added one equivalent HCl-saturated ether. White crystals of the desired compound was obtained. The crystals were filtered, washed on the filters with ether and dried. Yield 190 mg (65%). Mp. 136°-138° C. [α]D20 (C=1.5 MeOH) (-)7.6°.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customAfter removal of the solvent
  4. distillationby distillation
  5. dissolutionthe residual oil was dissolved in ether (50 ml)
  6. customA theoretical quantity of tetrabutylammonium iodide was precipitated
  7. filtrationThe precipitate was filtered off and to the filtrate

Sources & evidence

ORD record
ord-376e528b4a1b46c183939a1db3829d30
Source dataset
uspto-grants-1988_01
Patent number
US04719219

Reaction notes

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