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

HRID 247991
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HRID 247991 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매

2
HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-de674513d9f14c068d572eadc9d5a65e
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05208247

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