Sodium Iodide → 3-(Piperidin-1-yl)propyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 57216

反応式

HRID 57216 の反応式
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26]Cl)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH:28]1[CH2:33][CH2:32]O[CH2:30][CH2:29]1.[I-].[Na+].[CH3:36]N(C)C=O>>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26][N:28]2[CH2:33][CH2:32][CH2:36][CH2:30][CH2:29]2)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

5

反応物 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8083MorpholineHCID 668698443-Chloropropyl 5-(tetradecyloxy)furan-2-carboxylate

生成物 1

HCID 668696673-(Piperidin-1-yl)propyl 5-(tetradecyloxy)furan-2-carboxylate

反応条件

温度
55 °C

実験手順

To a solution of the above prepared 3-chloropropyl 5-(tetradecyloxy)furan-2-carboxylate (0.272 g, 0.68 mmol) in 6 mL of N,N-dimethylformamide was added morpholine (0.535 mL, 6.1 mmol) and sodium iodide (10 mg). The resulting solution was stirred at 55° C. for 36 hrs at which time HPLC analysis of the reaction mixture indicated near complete consumption of the starting material. The solution was diluted with EtOAc (30 mL), brine (10 mL) and water (10 mL) such that both phases were clear solutions. The phases were separated and the organic phase was washed with water (20 mL) and brine (20 mL) and then dried and concentrated. The crude material was purified by flash chromatography eluting with 5-40% EtOAc in hexanes to yield 0.217 g of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.10 (d, 1H), 5.30 (d, 1H), 4.30 (t, 2H), 4.10 (t, 2H), 3.7 (t, 4H), 2.40-2.50 (m, 6H), 1.90 (p, 2H), 1.76 (p, 2H), 1.18-1.50 (m, 22H), 0.89 (t, 3H).

後処理

  1. customindicated near complete consumption of the starting material
  2. additionThe solution was diluted with EtOAc (30 mL), brine (10 mL) and water (10 mL) such that both phases
  3. customThe phases were separated
  4. washthe organic phase was washed with water (20 mL) and brine (20 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography
  8. washeluting with 5-40% EtOAc in hexanes

出典と根拠

ORDレコード
ord-2287f33b86d64e2ea5c6e6f595650d9b
出典データセット
uspto-grants-2016_09
特許番号
US09434718B2

関連ノート

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