4-Fluorobenzylamine → Bis(4-fluorobenzyl)aMine, 97%

HRID 392827ノート

反応式

HRID 392827 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([F:10])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 673264-FluorobenzylamineHCID 680214-Fluorobenzyl bromide

生成物 1

HCID 834401Bis(4-fluorobenzyl)aMine, 97%収率 98.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 4-flourobenzylamine (1.17 g, 9.4 mmol) dissolved in 5 mL of THF was added 4-fluorobenzyl-bromide (0.88 g, 4.7 mmol) dropwise. The reaction was stirred overnight resulting in the formation of a white solid. After filtering off the solid solvent was removed to yield 1.08 g crude di-(4-fluorobenzyl) amine. To this was added 19 mL of CH2Cl2 and 19 mL of saturated (aq.) NaHCO3. Acetyl chloride (0.67 mL, 9.4 mmol) was added to the rapidly stirring mixture and the reaction allowed to proceed overnight. The mixture was diluted with CH2Cl2, transferred to a separatory funnel. The organic layer was separated, washed with satd (aq.) NaCl, dried over Na2SO4 and the solvent removed to yield 1.01 g oil. The product was purified by column chromatography (4×7 cm SiO2, 20-40% EtOAc/Hexanes) to yield 603 mg (55% yield) oil. LC/MS (M+H) calcd for C14H14NF2: 276.12, found: 276.13. HRMS (M+H) calcd for C14H14NF2: 276.1200, found: 276.1192. Anal calcd for C16H15F2NO: C, 69.80; H, 5.49; N, 5.08; found: C, 59.53; H, 5.41; N, 5.06. 1H NMR (500 MHz, DMSO) δ: 2.10 (s, 3), 4.45 (s, 2), 4.49 (s, 2), 7.18-7.27 (m, 8). 13C NMR (125 MHz, DMSO) δ; 21.34, 47.04, 50.04, 114.90, 115.07, 115.27, 115.45, 128.51, 128.58, 129.57, 129.64, 133.32, 133.34, 133.86, 133.89, 160.25, 160.33, 162.17, 162.27, 170.22.

後処理

  1. customresulting in the formation of a white solid
  2. filtrationAfter filtering off the solid solvent
  3. customwas removed

出典と根拠

ORDレコード
ord-2850a09dc08c451689523c9af810fdff
出典データセット
uspto-grants-2004_10
特許番号
US06803378B2

反応ノート

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