Hydrochloric Acid → 4,4,4-trifluoro-2-methylbutan-1-amine hydrochloride

HRID 1975425ノート

反応式

HRID 1975425 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:9]([NH2:11])=O.[ClH:17]>C(OCC)C>[ClH:17].[CH3:7][CH:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:9][NH2:11]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 100805982-Methyl-4,4,4-trifluorobutyramideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 218411224,4,4-trifluoro-2-methylbutan-1-amine hydrochloride収率 141.3%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of lithium aluminum hydride (15.5 g) in diethyl ether (290 ml) was added a solution of 2-methyl-4,4,4-trifluorobutyramide (31.74 g) in diethyl ether (0.5 L) at a rate to obtain a gentle reflux. After heating at reflux for 12 hours and cooling to 0° C., the reaction was quenched with saturated sodium sulfate solution and allowed to warm to ambient temperature. The mixture was dried (Na2SO4) and filtered through diatomaceous earth with diethyl ether wash. The filtrate was treated with gaseous hydrochloric acid (14.9 g, 0.409 mol) and then the solvent was evaporated. The residue was dissolved in methylene chloride and combined with product from a similar reaction of 2-methyl-4,4,4-trifluorobutyramide (25 g). Recrystallization from methylene chloride and diethyl ether, followed by trituration with ethyl acetate, afforded 2-methyl-4,4,4-trifluorobutylamine hydrochloride (51.35 g, 79%) as a light pink solid; mp 224.5°-225.5° C.; MS(CI): 142 (M+H-HCl). Analysis for C5H11ClF3N: Calculated: C, 33.81; H, 6.24; N, 7.89. Found: C, 33.93; H, 6.13; N, 8.17.

後処理

  1. customto obtain a gentle reflux
  2. temperatureAfter heating
  3. temperatureat reflux for 12 hours
  4. customthe reaction was quenched with saturated sodium sulfate solution
  5. temperatureto warm to ambient temperature
  6. dry with materialThe mixture was dried (Na2SO4)
  7. filtrationfiltered through diatomaceous earth with diethyl ether
  8. washwash
  9. customthe solvent was evaporated
  10. dissolutionThe residue was dissolved in methylene chloride
  11. customcombined with product from a similar reaction of 2-methyl-4,4,4-trifluorobutyramide (25 g)
  12. customRecrystallization from methylene chloride and diethyl ether

出典と根拠

ORDレコード
ord-35a9c5ed1c6046029fceeaa480e06c44
出典データセット
uspto-grants-1994_02
特許番号
US05286740

反応ノート

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