Sodium Hydroxide → 3-(4-Chlorophenoxy)propan-1-amine

HRID 361715

反応式

HRID 361715 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Al+3].[Li+].[Cl-].[Cl-].[Cl-].[Cl:11][C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][CH2:18][C:19]#[N:20])=[CH:14][CH:13]=1.[OH-].[Na+]>CCOCC.O>[Cl:11][C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][CH2:18][CH2:19][NH2:20])=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 96550Propionitrile, 3-(p-chlorophenoxy)-HCID 166981Aluminum;lithium;tetrachlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 64846543-(4-Chlorophenoxy)propan-1-amine収率 183.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒3 回

実験手順

A suspension of aluminium chloride (7.95 g) in ether (25 ml) was added to a stirred suspension of lithium aluminium chloride (2.02 g) in ether (45 ml). A solution of 3-(4-chlorophenoxy)propionitrile (10. 4 g) in ether (75 ml) was then added to the stirred suspension in a dropwise fashion over a period of 0.5 hours. The reaction mixture was allowed to reflux during the addition and was stirred for a further 0.75 hours after the addition was complete. Water (20 ml) was slowly added to the cooled reaction mixture, followed by sodium hydroxide solution (0.001M, 10 ml). The resulting precipitate was collected by filtration, washed with ethyl acetate and the filtrate dried using phase separating paper and evaporated to give 3-(4-chlorophenoxy)propylamine as an oil (7.5 g). Treatment of this oil with ethereal hydrogen chloride solution gave a solid which was recrystallised from ethanol to yield the hydrogen chloride salt of 3-(4-chlorophenoxy)propylamine as a solid (1.6 g), m.p. 182° C.; microanalysis, found: C, 48.5; H, 5.9; N, 6.3, Cl 31.6%; C9H12ONCl.HCl requires: C, 48.6; H, 5.9; N, 6.3; Cl, 32.0%.

後処理

  1. temperatureto reflux during the addition
  2. additionafter the addition
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with ethyl acetate
  5. customthe filtrate dried
  6. customseparating paper
  7. customevaporated

出典と根拠

ORDレコード
ord-47744fe93c224c44815e5fcf44026a0d
出典データセット
uspto-grants-1999_02
特許番号
US05866611

関連ノート

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