Sodium Chloride → Arecoline

HRID 35151Notes

Reaction equation

HRID 35151 reaction equation
[CH3:1][N:2]1[CH2:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH2:4][CH2:3]1.Br.[OH-].[K+].[Na+].[Cl-]>O>[CH3:1][N:2]1[CH2:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 9301Arecoline HydrobromideHCID 14797Potassium Hydroxide

Product 1

HCID 2230Arecoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ten grams of arecoline HBr was dissolved in a minimal quantity (approximately 25 ml) of water and adjusted to pH 10 with saturated KOH in a separatory funnel. One hundred mls of petroleum ether was added and the layers were mixed. NaCl was then added to saturate the aqueous layer. The organic layer was collected, and the aqueous layer was extracted three more times with petroleum ether. The combined organic layers were transferred to a 500 ml round bottom flask, boiling chips were added and the petroleum ether was removed by distillation. The remaining oil was layered with N2 and stored in low-actinic glassware. The oil was anlyzed by NMR to show the absence of a halogen component.

Workup

  1. additionthe layers were mixed
  2. concentrationto saturate the aqueous layer
  3. customThe organic layer was collected
  4. extractionthe aqueous layer was extracted three more times with petroleum ether
  5. customThe combined organic layers were transferred to a 500 ml round bottom flask
  6. additionwere added
  7. customthe petroleum ether was removed by distillation

Sources & evidence

ORD record
ord-2e83975f0e96488ea92c443cccb3aac6
Source dataset
uspto-grants-1988_08
Patent number
US04765985

Reaction notes

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