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

HRID 1110041ノート

反応式

HRID 1110041 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6f0f24f9548e40079c37b80cde3f3ab0
出典データセット
uspto-grants-1994_06
特許番号
US05324733

反応ノート

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