Ammonium Chloride → 2'-(2-Aminoethyl)spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] dihydrochloride

HRID 1758528ノート

反応式

HRID 1758528 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:9][N:10]1[CH2:19][C:18]2([CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)#[N:8].[Cl-:28].[NH4+]>O1CCCC1.CCOCC>[ClH:28].[ClH:28].[NH2:8][CH2:7][CH2:9][N:10]1[CH2:19][C:18]2([CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 132645362'-Cyanomethylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline]HCID 21226445Aluminium lithium hydride

生成物 1

HCID 159174782'-(2-Aminoethyl)spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] dihydrochloride収率 67.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred suspension of lithium aluminum hydride (5.3 g) in dry tetrahydrofuran (100 ml) at 0°, is added a solution of 2'-cyanomethylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (9.5 g) in dry tetrahydrofuran (50 ml). The mixture is heated to reflux for three hours. The mixture is cooled with an ice-bath, diluted with dry ether (300 ml) and saturated ammonium chloride solution (60 ml) is added in small portions over a period of one hour. The organic layer is collected, washed with water (2x) and dried over anhydrous magnesium sulfate. After filtering, the solvents are evaporated to an oil (7.3 g). The oil (3.7 g) is dissolved in ether and converted to dihydrochloride salt. The material is recrystallized twice from methanol/acetone/ether to yield product (3.0 g, 67.5%) as a solid, mp 158° (dec).

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux for three hours
  3. temperatureThe mixture is cooled with an ice-bath
  4. additionis added in small portions over a period of one hour
  5. customThe organic layer is collected
  6. washwashed with water (2x)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe solvents are evaporated to an oil (7.3 g)
  10. dissolutionThe oil (3.7 g) is dissolved in ether
  11. customThe material is recrystallized twice from methanol/acetone/ether

出典と根拠

ORDレコード
ord-964f192238974e3fbba175efe20cda7e
出典データセット
uspto-grants-1983_02
特許番号
US04374137

反応ノート

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