Hydrochloric Acid → N-stearyl pyridone

HRID 51196

反応式

HRID 51196 の反応式
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]([CH2:22][C:23]([O:25]CC)=O)#N.[C:28](OCC)(=O)[CH2:29]C(C)=O.N1CCCCC1.Cl>O.CO.COCCOC.C1(C)C=CC=CC=1>[CH2:1]([N:19]1[CH:29]=[CH:28][CH:20]=[CH:22][C:23]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 15793Octadecylamine

生成物 1

HCID 21388044N-stearyl pyridone収率 87.1%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

Into a 2 liter flask equipped with magnetic stir bar and temperature thermostat was charged octadecylamine (stearylamine, 18.9 grams, 0.07 mol; obtained from Sigma-Aldrich Co., Milwaukee, Wis.) followed with ethyl cyanoacetate (7.9 grams, 0.07 mol, density 1.06 grams per milliliter; obtained from Spectrum Chemicals, New Brunswick, N.J.). The resulting mixture was stirred and heated to 120° C. internal temperature for 1 hour, during which time a liquid byproduct was distilled away. To the hot reaction mixture was then sequentially added ethyl acetoacetate (10.08 grams, 0.0775 mol, density 1.02 grams per milliliter; obtained from Lonza Group, Germany), piperidine (11.0 grams, 0.13 mol, density 0.861 grams per milliliter; obtained from Sigma-Aldrich Co.), and a solvent mixture (60 milliliters) containing 5 parts by weight toluene and 1 part by weight 1,2-dimethoxyethane. The reaction proceeded with stirring at 120° C. for another 24 hours. The solvents were then distilled off in vacuo, and the remaining viscous solution was carefully poured into a stirring solution of methanol (80 milliliters), deionized water (20 milliliters), and concentrated hydrochloric acid (16 milliliters, 2.5 mol). A solid precipitate formed instantly and the slurry was vacuum filtered followed by rinsing of the solid cake with 2×50 milliliter portions of 80 percent aqueous methanol. The cake thus obtained was air-dried for 24 hours to afford 24.5 grams (0.061 mol, 87 percent yield) of N-stearyl pyridone product as light tan powder.

後処理

  1. customInto a 2 liter flask equipped with magnetic stir bar
  2. distillationduring which time a liquid byproduct was distilled away
  3. stirringwith stirring at 120° C. for another 24 hours
  4. distillationThe solvents were then distilled off in vacuo
  5. customA solid precipitate formed instantly
  6. filtrationfiltered
  7. washby rinsing of the solid cake with 2×50 milliliter portions of 80 percent aqueous methanol
  8. customThe cake thus obtained
  9. customwas air-dried for 24 hours

出典と根拠

ORDレコード
ord-b5639a1778f0486cbbabf1b2a80db971
出典データセット
uspto-grants-2004_03
特許番号
US06713614B2

関連ノート

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