Sulfuric Acid → N-ethyltetrahydro-2H-pyran-4-amine

HRID 650867노트

반응식

HRID 650867 반응식
S(=O)(=O)(O)O.[CH2:6]([NH2:8])[CH3:7].[O:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.[Na]>CO>[CH2:6]([NH:8][CH:12]1[CH2:13][CH2:14][O:9][CH2:10][CH2:11]1)[CH3:7]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 6341EthylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5360545Sodium

생성물 1

HCID 10964527N-ethyltetrahydro-2H-pyran-4-amine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

At 0° C. and with efficient cooling, 51 g (0.5 mol) of conc. sulfuric acid were added dropwise to a solution of 105 g (2.3 mol) of ethylamine in 0.5 l of methanol. 50 g (0.5 mol) of tetrahydro-2H-pyran-4-one and 18.8 g (0.3 mol) of sodium cyanoborhydride were then added successively. After 16 hours at room temperature, the methanol was distilled off, an excess of 10% strength aqueous sodium hydroxide solution was added and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were washed neutral with water, dried over magnesium sulfate and filtered and the residue was distilled. Bp. 76-82° C. (20 mbar), yield 24 g. 1H NMR (250 MHz, in CDCl3): δ=0.86 (s, 1H), 1.13 (t, 3H), 1.40 (dq, 2H), 1.84 (m, 2H), 2.68 (m, 3H), 3.40 (dt, 2H), 3.98 (m, 2H).

후처리

  1. distillationthe methanol was distilled off
  2. additionan excess of 10% strength aqueous sodium hydroxide solution was added
  3. extractionthe aqueous phase was extracted three times with dichloromethane
  4. washThe combined organic phases were washed neutral with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. distillationthe residue was distilled

출처 및 근거

ORD 기록
ord-adfa32b3afdb4153819d84692425decc
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06277790B1

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