2-Fluorobenzoyl chloride → 90183-00-9

HRID 1606917ノート

反応式

HRID 1606917 の反応式
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([Cl:15])=[O:14].[OH-].[NH4+].[OH-].[Na+]>CCOCC.CO.O>[ClH:15].[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[CH:2]([NH:1][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=1[F:10])[CH2:3]2

参加物

8

反応物 4

HCID 98082-Fluorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 1232383-Aminoquinuclidine2 回

生成物 1

HCID 2483427690183-00-9収率 64.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

In a closed system, a solution of 3-aminoquinuclidine (2.52 g, 0.020 mole) in 10 ml anhydrous ether was added dropwise to a stirred solution of 2-fluorobenzoyl chloride (3.13 g, 0.020 mole) in 100 ml anhydrous ether. After the addition was complete, the mixture was stirred another hour and the solid product (as the hydrochloride salt) was collected by filtration under nitrogen to give 4.75 g (84%). TLC analysis (3% conc. ammonium hydroxide in methanol) showed the presence of 3-aminoquinuclidine. The salt was dissolved in 10 ml water, basified with 6N sodium hydroxide solution, and extracted three times with 50 ml portions of methylene chloride. The combined extract was dried over magnesium sulfate and concentrated to give 3.67 g of the product as the free base. Recrystallization from toluene-isooctane gave 2.33 g of a white solid (some toluene insoluble material was removed by decanting the hot toluene solution). The solid free base was dissolved in 10 ml methanol, treated with excess ethereal hydrogen chloride and 100 ml isopropyl ether was added. The salt separated from solution as an oil, but crystallized on trituration. The white solid was collected under nitrogen to give 2.60 g; m.p. 233°-234° C. Mass spectrum (E.I.) m/e (% relative intensity): 248 (15), 125 (13), 123 (100), 109 (80), 96 (24), 95 (45), 84 (14), 75 (19), 70 (64), 42 (44), 41 (18).

後処理

  1. additionAfter the addition
  2. filtrationthe solid product (as the hydrochloride salt) was collected by filtration under nitrogen
  3. customto give 4.75 g (84%)
  4. extractionextracted three times with 50 ml portions of methylene chloride
  5. extractionThe combined extract
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-7b4a6415c112444fa0e60f9701bc9845
出典データセット
uspto-grants-1989_09
特許番号
US04863919

反応ノート

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