Sodium Chloride → 5-bromo-2,3-dihydro-1H-inden-2-amine

HRID 1531292ノート

反応式

HRID 1531292 の反応式
Br.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:12])[CH2:6]2.C(OC(C)C)(=O)C.[OH-].[Na+].[Cl-].[Na+]>O>[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:12])[CH2:6]2

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 7915Isopropyl AcetateHCID 14798Sodium HydroxideHCID 121920575-Bromo-2,3-dihydro-1H-inden-2-amine--hydrogen bromide (1/1)

生成物 1

HCID 112987955-bromo-2,3-dihydro-1H-inden-2-amine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
22.5 °C

実験手順

A solution of 118.8 g of 2-aminoindane hydrochloride in 594 mL of water is heated to a temperature of 58-60° C. and 120.0 g of bromine is added over a period of 50 minutes while maintaining an internal temperature at 58 to 62° C. The mixture is stirred at 60-62° C. for 1 hour and 107 mL of hydrobromic (48%) is added over a period of 5 minutes while maintaining the internal temperature of 60-62° C. The mixture is stirred for an additional 10 minutes. The reaction mixture is cooled to an internal temperature of 20-23° C. over a period of 1 hour. The resulting solid is collected by filtration, washed with 3×133 mL of 2-propanol and dried at 58-60° C. under vacuum (10-30 torr) to obtain crude (±)-5-bromo-2-aminoindan hydrobromide. A suspension of 156.0 g of crude (±)-5-bromo-2-aminoindane hydrobromide in 390 mL of deionized water is heated to a temperature at 95-100° C. to obtain a clear solution. The solution is cooled to an internal temperature at 20-23° C. over a period of 2.5 hours and stirred at 20-23° C. for an additional 30 minutes. The resulting solid is collected by filtration and washed with 3×20 mL of water (precooled to 0-5° C.), and dried at 60-65° C. under vacuum (10-30 torr) with nitrogen bleeding to obtain (±)-5-bromo-2-aminoindane hydrobromide. A mixture of 130.0 g of (±)-5-bromo-2-aminoindane hydrobromide and 1500 mL of isopropyl acetate is stirred at 20-25° C. under nitrogen. A solution (precooled to 20-25° C.) of 26.62 g of sodium hydroxide and 186.35 g of sodium chloride in 750 mL of water is added over a period of 5 minutes while maintaining an internal temperature at 20-25° C. The suspension is stirred efficiently until all the solid dissolves (30 minutes). The organic layer is separated and the aqueous layer is extracted with 750 mL of isopropyl acetate. The organic layers are combined to afford ˜2330 mL of a solution of (±)-5-bromo-2-aminoindane free base.

後処理

  1. temperaturewhile maintaining an internal temperature at 20-25° C
  2. stirringThe suspension is stirred efficiently until all the solid
  3. dissolutiondissolves (30 minutes)
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted with 750 mL of isopropyl acetate

出典と根拠

ORDレコード
ord-c570b7c03ae84e8ab512c00c6f35cc57
出典データセット
uspto-grants-2001_03
特許番号
US06197798B1

反応ノート

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