Sodium Iodide → (r)-5,11-Dihydro-5-[1-(3-pyrrolidinophenethyl)pyrrolidin-2-ylmethyl]dibenzo[b,e][1,4]oxazepine

HRID 2251900노트

반응식

HRID 2251900 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][O:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.S(O[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:30]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[N:35]1([C:31]2[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=2)[CH2:28][CH2:27][N:1]2[CH2:5][CH2:4][CH2:3][C@@H:2]2[CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][O:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)[CH2:39][CH2:38][CH2:37][CH2:36]1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 22934159HCID 22934159, 화합물HCID 69200761(r)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine

생성물 1

HCID 12990604(r)-5,11-Dihydro-5-[1-(3-pyrrolidinophenethyl)pyrrolidin-2-ylmethyl]dibenzo[b,e][1,4]oxazepine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
90 °C

실험 절차

(R)-5,11-dihydro-5-(2-pyrrolidylmethyl)dibenzo[b,e][1,4]oxazepine (240 mg, 0.85 mmol, prepared by a method disclosed in International Patent No. 9912925A1), 3-pyrrolidinophenethyl mesylate (253 mg, 0.94 mmol), sodium carbonate (106 mg, 1.0 mmol) and sodium iodide (10 mg, 0.07 mmol) were added to acetonitrile (20 ml), and they were heated at 90° C. under reflux for 6.5 hours. The solvent was evaporated under reduced pressure, and the residue was distributed into ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with water and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was subjected to the silica gel column chromatography. After the elution with hexane and ethyl acetate (15:1) and then with hexane and ethyl acetate (2:1) as the eluent, suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (R)-5,11-dihydro-5-[1-(3-pyrrolidinophenethyl)pyrrolidin-2-ylmethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oily substance (208 mg, 54%).

후처리

  1. temperatureunder reflux for 6.5 hours
  2. customThe solvent was evaporated under reduced pressure
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washAfter the elution with hexane and ethyl acetate (15:1)
  7. customwith hexane and ethyl acetate (2:1) as the eluent, suitable fractions were collected
  8. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-787dce2ebfce4ceaba7b45924fc18f83
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320973B2

반응 노트

불러오는 중…