Water → N-Ethylpyridine-4-methylamine

HRID 874197노트

반응식

HRID 874197 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH2:9]([NH2:11])[CH3:10].[BH4-].[Na+].O>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:11][CH2:9][CH3:10])=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6341EthylamineHCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 96681N-Ethylpyridine-4-methylamine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

15.70 g (0.147 mol) of 4-pyridine-formaldehyde was dissolved in 200 mL of ethanol, added under stirring in cold-water-bath with 21 g (0.296 mol) of 65-70% ethylamine aqueous solution, reacted for 0.5 h, monitored with TLC until the reaction was almost completed. Added carefully with 5.6 g (0.148 mol) of sodium borohydride in several batches, small amount in each batch, after the end of addition, added with 30 mL of water, reacted overnight (20 h), the reaction was completed according to TLC monitoring. Evaporated to remove solvent, added with water, extracted with dichloromethane, washed with water and saturated saline in order, dried with anhydrous sodium sulfate, evaporated to remove solvent to obtain yellow thick liquid, 30 g, crude yield 73.4%. 1H NMR(CDCl3, 400 MHz)δ: 1.14(t, 3H, J=7.00 Hz), 2.66(q, 2H, J=7.00 Hz), 3.81(s, 2H), 7.26-7.27(m, 2H), 8.52-8.54(m, 2H).

후처리

  1. additionadded
  2. customreacted for 0.5 h
  3. additionafter the end of addition
  4. customreacted overnight (20 h)
  5. customEvaporated
  6. customto remove solvent
  7. additionadded with water
  8. extractionextracted with dichloromethane
  9. washwashed with water and saturated saline in order
  10. dry with materialdried with anhydrous sodium sulfate
  11. customevaporated
  12. customto remove solvent
  13. customto obtain yellow thick liquid, 30 g, crude yield 73.4%

출처 및 근거

ORD 기록
ord-280a2856eaed4904b56db681a40302d7
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980887B2

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