Arecoline Hydrobromide → Norarecoline Hydrochloride

HRID 736789ノート

反応式

HRID 736789 の反応式
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

参加物

6

反応物 3

HCID 9301Arecoline HydrobromideHCID 10340Sodium CarbonateHCID 94429Triphosgene

生成物 1

HCID 201540Norarecoline Hydrochloride

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
57.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b979d331efa04ccaabbbfed0ec26ddd5
出典データセット
uspto-grants-2009_09
特許番号
US07595327B2

反応ノート

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