Water → 1-{4-[(3-Fluorobenzyl)oxy]phenyl}methanamine

HRID 1425695노트

반응식

HRID 1425695 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.O.[OH-].[Na+]>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 22293834-[(3-Fluorophenyl)methoxy]benzonitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 167723641-{4-[(3-Fluorobenzyl)oxy]phenyl}methanamine수율 86.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

(Aldrich data.) To a LiAlH4 (5.02 g, 132.0 mmol) suspension in THF (400 mL) was added dropwise a THF (30 mL) solution of 4-(3-fluorobenzyloxy)benzonitrile (10.00 g, 44.0 mmol) at 0° C. The mixture was stirred at room temperature (16 h) and H2O (4 mL) was added dropwise at 0° C. followed by an aqueous NaOH solution (2 mL, 15% w/w), and then H2O (4 mL). The mixture was stirred at room temperature (2 h), and the precipitate filtered through a Celite® pad and the pad washed with CH2Cl2. The filtrate was concentrated in vacuo to obtain a white solid (8.82 g, 86%): Rf=0.00 (hexanes/EtOAc 9/1); 1H NMR (CDCl3) δ 1.61 (br s, NH2), 3.79 (s, CH2NH2), 5.04 (s, CH2O), 6.90-7.04 (m, 3 ArH) 7.13-7.37 (m, 5 ArH); HRMS (M−NH2+)(ESI+) 215.088 [M−NH2+] (calcd for C14H12O+ 215.087).

후처리

  1. additionwas added dropwise at 0° C.
  2. filtrationthe precipitate filtered through a Celite® pad
  3. washthe pad washed with CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-5447094e6a8247878088e5df2386a457
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933065B2

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