Acetonitrile → 2-Methyl-2,3-dihydro-5-benzo[b]furanyl-2-[4-(p-chlorophenyl)butylamino]-1-propanol

HRID 980503노트

반응식

HRID 980503 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[BH4-].[Na+].[OH-:21].[Na+].[C:23](#N)[CH3:24]>O>[CH3:10][CH:9]1[O:21][C:4]2[CH:3]=[CH:2][C:7]([CH:13]([OH:16])[CH:23]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH3:24])=[CH:6][C:5]=2[CH2:8]1

참가 물질

7

반응물 5

HCID 6342Acetonitrile2회HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 107738224-(4-Chlorophenyl)butan-1-amine

생성물 1

HCID 137852402-Methyl-2,3-dihydro-5-benzo[b]furanyl-2-[4-(p-chlorophenyl)butylamino]-1-propanol수율 31%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 8.2 gr. (45 moles) of p-chlorophenylbutylamine in 100 ml of acetonitrile is stirred and refluxed. 12.4 gr. (90 mmoles) of potassium carbonate are added thereto, then over one hour a solution of 12 gr. (45 mmoles) of the preceding brominated cetone in 80 ml of acetonitrile. After the end of the addition, reflux is maintained for 1.5 hour. To the medium at room temperature, a solution of 1.8 gr. (48 mmoles) of sodium borohydride in 10 ml of water basified with a drop of 40% aqueus NaOH is dropwise added. The solid is filtered and the filtrate is dry evaporated. The residue is a solid. The latter added to the first one is recrystallized from a 1:1 hexane/cyclohexane mixture. 5.1 gr. (14 mmoles, 31%) of a product are obtained, the melting point of which being 107.8° C. The NMR spectrum confirms the expected structure.

후처리

  1. temperaturerefluxed
  2. additionAfter the end of the addition
  3. temperaturereflux
  4. temperatureis maintained for 1.5 hour
  5. customat room temperature
  6. additionis dropwise added
  7. filtrationThe solid is filtered
  8. customthe filtrate is dry
  9. customevaporated
  10. additionThe latter added to the first one
  11. customis recrystallized from a 1:1 hexane/cyclohexane mixture

출처 및 근거

ORD 기록
ord-6d5798c34bdc48d6b2ca3a0191ca2d35
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04638070

반응 노트

불러오는 중…