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3-Pyridinecarboxaldehyde → N-[4-(Tetradecyloxy)phenyl]-3-pyridinemethanamine

HRID 247991
ノート
印刷プレビュー

反応式

HRID 247991 の反応式
[CH2:1]([O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[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].Cl.CO.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=O)[CH:27]=1.C([BH3-])#N.[Na+].[OH-].[K+]>O.CO>[CH2:1]([O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][CH2:32][C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 103713-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 191002p-(n-Tetradecyloxy)phenylamineHCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanol

生成物 1

HCID 19015436N-[4-(Tetradecyloxy)phenyl]-3-pyridinemethanamine収率 76.4%

試薬・触媒・溶媒

2
HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a room temperature slurry of 7.26 g of product from Example 82, 60 ml of methyl alcohol and 9.5 ml of 5N hydrochloric acid/methanol is added, dropwise, 2.55 g of 3-pyridinecarboxaldehyde. After 10 minutes, a total of 1.64 g of sodium cyanoborohydride is very carefully added in 3 separate portions over 1.5 hours. The initial reaction is vigorous. The reaction mixture is stirred at room temperature for 68 hours, diluted with water, made basic with potassium hydroxide and extracted with methylene chloride. The methylene chloride extract is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 90% ethyl acetate/hexane) to give 7.2 g of the desired product as colorless crystals.

後処理

  1. customseparate portions over 1.5 hours
  2. customThe initial reaction
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washis washed with saturated sodium chloride
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (silica gel: 90% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-de674513d9f14c068d572eadc9d5a65e
出典データセット
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05208247

反応ノート

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