Acetic Acid → 5-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine

HRID 1166409

반응식

HRID 1166409 반응식
[Cl:1][CH2:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=O.[BH4-].[Na+].C(O)(=O)C.O>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 6069615-(3-Chloropropanoyl)-10,11-dihydro-5H-dibenzo[b,f]azepineHCID 4311764Sodium borohydride2회

생성물 1

HCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine수율 38.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-chloro-1-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propanone (14.0 g, 0.044 mol) in tetrahydrofuran (150 ml) at 0° C., sodium borohydride (6.66 g, 0.176 mol) was added, followed by dropwise addition of glacial acetic acid (10.0 ml), The resulting mixture was stirred at room temperature overnight and then heated at reflux temperature for 2 h. More sodium borohydride (6.50 g, 172 mmol) and then borontrifluoride diethyl etherate (20.0 ml, 0.163 mol) were added and heating at reflux temperature was continued for 20 h. Water (350 ml) was cautiously added and the phases were separated. The aqueous phase was extracted with toluene (3×100 ml). The combined organic phases were washed with brine (3×100 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (100 g) using a gradient of heptane and ethyl acetate (10:0→10:2), to give 4.58 g (38%) of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oil.

후처리

  1. temperatureheated
  2. temperatureat reflux temperature for 2 h
  3. temperatureheating
  4. temperatureat reflux temperature
  5. waitwas continued for 20 h
  6. customthe phases were separated
  7. extractionThe aqueous phase was extracted with toluene (3×100 ml)
  8. washThe combined organic phases were washed with brine (3×100 ml)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography on silica gel (100 g)

출처 및 근거

ORD 기록
ord-6fe6831ea2d246c5ab79d4a85c3bf98e
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613791B1

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