Potassium Carbonate → 2-allyl-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

HRID 865338노트

반응식

HRID 865338 반응식
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:6]=2[C:5]1=[O:16])[CH:2]=[CH2:3].[N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]OS(C1C(C)=CC=CC=1)(=O)=O)=[N+:18]=[N-:19].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[CH:12][C:13]([O:15][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:17]=[N+:18]=[N-:19])=[CH:14][C:6]=2[C:5]1=[O:16])[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 22905051HCID 22905051, 화합물HCID 86747262HCID 86747262, 화합물

생성물 1

HCID 229050032-allyl-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
65 °C

실험 절차

A suspension of 2-allyl-8-hydroxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (1.0 g, 0.0049 mol), 8-azido-1-(toluenesulfonyloxy)octane (1.50 g, 0.0049 mol) and K2CO3 in N,N-dimethylformamide (20 mL) was stirred vigorously under argon, and heated at 65° C. for 18 hours. The solution was then partitioned between ethyl acetate and brine, and the combined organic layers were washed with water, dried (K2CO3), filtered, and concentrated in vacuo. The residue was purified by chromatography over silica gel to yield 920 mg (51%) of 2-allyl-8-(8-azidooctyloxy)-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one as a colorless oil; 1H NMR(CDCl3) d7.47(s, 1H), 6.95(d, J=6 Hz, 1H), 6.84(dd, J=3, 6 Hz, 1H), 5.89(m, 1H), 5.22(m, complex, 2H), 4.20(d, J=6 Hz, 2H), 3.95(t, J=6 Hz, 2H), 3.22(t, J=6 Hz, 2H) 2.66(t, J=6 Hz, 2H), 1.90(t, J=6 Hz, 2H), 1.79(t, J=6 Hz, 2H), 1.60(m, 4H), 1.35(m, 6H).

후처리

  1. customThe solution was then partitioned between ethyl acetate and brine
  2. washthe combined organic layers were washed with water
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography over silica gel

출처 및 근거

ORD 기록
ord-bc605387433f4702b04e2652a3e990a5
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565449

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