Arecoline Hydrobromide → Norarecoline Hydrochloride

HRID 736789Notes

Reaction equation

HRID 736789 reaction equation
C[N:2]1[CH2:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH2:4][CH2:3]1.Br.C(=O)([O-])[O-].[Na+].[Na+].[Cl:19]C(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O.C1(C)C=CC=CC=1>[ClH:19].[NH:2]1[CH2:3][CH2:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH2:7]1

Participants

6

Reactant 3

HCID 9301Arecoline HydrobromideHCID 10340Sodium CarbonateHCID 94429Triphosgene

Product 1

HCID 201540Norarecoline Hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
57.5 °C

Procedure

Arecoline hydrobromide (25 g, 106 mmol) was neutralized with sodium carbonate (12.8 g, 120 mmol, 1.1 eq) in water (200 mL) for 30 min. The neutralized product was dissolved in toluene (50 mL) and added dropwise to a solution of triphosgene (16.3 g, 54.9 mmol, 0.52 eq) in toluene (100 mL) at 0° C. The resulting mixture was heated at 55-60° C. overnight. The reaction mixture was then concentrated in vacuo and the residue was dissolved in water (300 mL) and heated at 80° C. for 3 h. The water was evaporated and chased with toluene 3 times. The crude methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride, obtained as a thick brown oil, was used as is in the next reaction.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (300 mL)
  3. temperatureheated at 80° C. for 3 h
  4. customThe water was evaporated

Sources & evidence

ORD record
ord-b979d331efa04ccaabbbfed0ec26ddd5
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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