Hydrochloric Acid → (R)-1-(2,5-difluorophenoxy)-2-propanamine hydrochloride

HRID 1633838ノート

反応式

HRID 1633838 の反応式
[F:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH2:5][C@H:6]([N:8]1C(=O)C2C(=CC=CC=2)C1=O)[CH3:7].NN.[ClH:26]>C(O)C.C(OCC)(=O)C.CCOCC>[ClH:26].[F:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH2:5][C@H:6]([NH2:8])[CH3:7]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 69472648(R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione

生成物 1

HCID 69476187(R)-1-(2,5-difluorophenoxy)-2-propanamine hydrochloride

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To 5.4 g (R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione in 250 mL absolute ethanol was added 6.0 mL hydrazine. The solution was heated to reflux for 100 minutes. A white precipitate formed. The reaction was allowed to cool to room temperature and was filtered to remove the precipitate. Concentration of the filtrate gave a gummy paste which was taken up in ethyl acetate and washed once with brine and twice with 100 mL 1N hydrochloric acid. The combined acidic aqueous layers were basified with 1N sodium hydroxide and extracted three times with ethyl acetate. The combined organic extracts were dried and the solvent was removed to afford an oil. The oil was diluted with dry ether and 30 mL of 1N hydrochloric acid in ether was added. The resulting white precipitate was collected by filtration and dried to give the title compound of Step B as a white powder: mp 127-130° C., 1H NMR (Me2SO-d6) δ1.30 (d, 3H), 3.60 (m, 1H), 4.22 (m, 2H), 6.80 (m, 1H), 7.22 (m, 2H), 8.30 (br s, 3H).

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux for 100 minutes
  3. customA white precipitate formed
  4. filtrationwas filtered
  5. customto remove the precipitate
  6. customConcentration of the filtrate gave a gummy paste which
  7. washwashed once with brine and twice with 100 mL 1N hydrochloric acid
  8. extractionextracted three times with ethyl acetate
  9. customThe combined organic extracts were dried
  10. customthe solvent was removed
  11. customto afford an oil
  12. additionwas added
  13. filtrationThe resulting white precipitate was collected by filtration
  14. customdried

出典と根拠

ORDレコード
ord-3e403d4fc63440df9c534735e51ce75a
出典データセット
uspto-grants-2003_01
特許番号
US06504058B1

反応ノート

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