Dipropylamine → Ropinirole

HRID 358823ノート

反応式

HRID 358823 の反応式
Br[CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH2:14]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16]>Cl>[CH2:14]([N:17]([CH2:18][CH2:19][CH3:20])[CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2)[CH2:15][CH3:16]

参加物

4

反応物 2

HCID 8902DipropylamineHCID 99918542H-Indol-2-one, 4-(2-bromoethyl)-1,3-dihydro-

生成物 1

HCID 5095Ropinirole収率 58.5%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

Under an atmosphere of nitrogen, a suspension of 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one (245 mg, 102 mmol) was prepared by the addition of di-n-propylamine (1.00 g, 10 mmol, 1.35 ml) which has previously been degassed with a stream of nitrogen. After stirring for 30 minutes, degassed acetonitrile (5 ml) was added to give a pale yellow solution. After an additional hour the solution was heated, and maintained at reflux for 5 hours. After cooling to ambient temperature, the solution was poured into IN hydrochloric acid (35 ml) and extracted with ether (50 ml). The aqueous layer was made neutral to pH 7-7.5 with solid sodium bicarbonate and extracted with dichloromethane (50 ml). After drying separately, the ether layer was evaporated to give 4-vinyl-indol-2-one (60 mg, 37.7%) Evaporation of the dichloromethane layer gave 4-[2-(dipropylamino)ethyl]-1.3-dihydro-2H-indol-2-one (155 mg. 58.5%) as free-base which was then taken up in absolute ethanol (5 ml) and saturated with gaseous hydrogen chloride. The solvent was removed in vaccuo to give the crude hydrochloride salt (170 mg) as a light yellow solid. Recrystallisation from absolute ethanol (2 ml) gave light yellow crystals (110 mg 63% from the free-base) of 4-[2-(dipropylamino)ethyl]-1,3- dihydro-2H-indol-2-one hydrochloride m.p. 242-244° C.

後処理

  1. customhas previously been degassed with a stream of nitrogen
  2. customdegassed acetonitrile (5 ml)
  3. additionwas added
  4. customto give a pale yellow solution
  5. temperatureAfter an additional hour the solution was heated
  6. temperaturemaintained
  7. temperatureat reflux for 5 hours
  8. extractionextracted with ether (50 ml)
  9. extractionextracted with dichloromethane (50 ml)
  10. customAfter drying separately
  11. customthe ether layer was evaporated
  12. customto give
  13. custom4-vinyl-indol-2-one (60 mg, 37.7%) Evaporation of the dichloromethane layer

出典と根拠

ORDレコード
ord-db94e617b55c479ead5bc0cd94882f8a
出典データセット
uspto-grants-1991_03
特許番号
US04997954

反応ノート

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