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

HRID 650867ノート

反応式

HRID 650867 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-adfa32b3afdb4153819d84692425decc
出典データセット
uspto-grants-2001_08
特許番号
US06277790B1

反応ノート

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