Benzyl Bromide → 1'-(Phenylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine]

HRID 1110041노트

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HRID 1110041 반응식
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([N:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 156376162,3-Dihydrospiro(indene-1,4'-piperidine)

생성물 1

HCID 46872381'-(Phenylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine]수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a stirred solution of spiro[indane-1,4'-piperidine] (110 mg, 0.59 mmol), in anhydrous DMF (10 ml), under an atmosphere of nitrogen, was added potassium carbonate (98 mg, 0.71 mmol) followed by benzyl bromide (0.08 ml, 0.65 mmol) dropwise. The mixture was heated at 100° C. for 2 hours, after which time the solution was cooled to ambient temperature. The solvent was removed in vacuo, then ether (20 ml) was added to the residue and the mixture was washed with water (2×20 ml). The organic layer was separated, dried (MgSO4) and the solvent evaporated in vacuo. The crude residue was chromatographed using 1:1 petrol (60/80):ether, to give 1'-benzylspiro[indane-1,4'-piperidine] as a viscous colourless oil (31 mg, 20%).

후처리

  1. temperatureafter which time the solution was cooled to ambient temperature
  2. customThe solvent was removed in vacuo
  3. additionether (20 ml) was added to the residue
  4. washthe mixture was washed with water (2×20 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated in vacuo
  8. customThe crude residue was chromatographed

출처 및 근거

ORD 기록
ord-6f0f24f9548e40079c37b80cde3f3ab0
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324733

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