Arecoline Hydrobromide → Norarecoline Hydrochloride

HRID 736789

반응식

HRID 736789 반응식
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

참가 물질

6

반응물 3

HCID 9301Arecoline HydrobromideHCID 10340Sodium CarbonateHCID 94429Triphosgene

생성물 1

HCID 201540Norarecoline Hydrochloride

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
57.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b979d331efa04ccaabbbfed0ec26ddd5
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595327B2

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