Water → 4-(((3-Fluoro)benzyloxy)methyl)benzylamine

HRID 73148

반응식

HRID 73148 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=1)[CH2:11][O:12][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.O.[OH-].[Na+]>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=1)[CH2:11][O:12][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 462235894-((3-Fluorobenzyloxy)methyl)benzonitrile

생성물 1

HCID 462235904-(((3-Fluoro)benzyloxy)methyl)benzylamine수율 37%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a LiAlH4 (2.00 g, 53.4 mmol) suspension in THF (300 mL) was added dropwise a THF (20 mL) solution of 4-(((3-fluoro)benzyloxy)methyl)benzonitrile (4.30 g, 17.8 mmol) at 0° C. The mixture was stirred at room temperature (16 h) and H2O (1.6 mL) was added dropwise at 0° C. followed by an aqueous NaOH solution (0.8 mL, 15% w/w), and then H2O (1.6 mL). The mixture was stirred at room temperature (2 h), and the precipitate filtered and washed with CH2Cl2. The filtrate was concentrated in vacuo and the solid triturated with Et2O to obtain a white solid (1.60 g, 37%). The solid was used in the next step with no other purification: Rf=0.00 (hexanes/EtOAc 8/2); mp >138° C. (decomp.); IR (nujol) 3224, 3100, 3039, 2970, 2843, 1593, 1520, 1456, 1375, 1257, 1143, 1073, 940, 866, 733, 686, 549 cm−1; 1H NMR (CDCl3) δ 3.87 (s, CH2NH2), 4.47-4.54 (m, 2 CH2O), 7.08-7.45 (m, 8 ArH); 13C NMR (CDCl3) δ 43.1 (CH2N), 70.4, 71.2 (2 CH2O), 113.8 (d, J=21.7 Hz, C2′ or C4′), 114.1 (d, J=20.5 Hz, C4′ or C2′), 123.1 (d, J=2.3 Hz, C6′), 127.5 (ArC), 128.1 (ArC), 130.2 (d, J=8.0 Hz, C5′), 137.2, 137.3 (2 ArC), 141.4 (d, J=6.8 Hz, C1′), 162.1 (d, J=242.5 Hz, C3′); HRMS (M+H+) (ESI+) 246.1294 [M+H+] (calcd for C15H16FNOH+ 246.1294).

후처리

  1. additionwas added dropwise at 0° C.
  2. filtrationthe precipitate filtered
  3. washwashed with CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe solid triturated with Et2O

출처 및 근거

ORD 기록
ord-7dca82492bfd46f99cb72431e8c9dab1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829033B2

연결된 노트

불러오는 중…