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

HRID 361715

반응식

HRID 361715 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 64846543-(4-Chlorophenoxy)propan-1-amine수율 183.4%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매3회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-47744fe93c224c44815e5fcf44026a0d
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866611

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