Potassium Carbonate → 5-[(3-Benzyl)-1-piperidinyl]valeric acid methyl ester

HRID 1861761ノート

反応式

HRID 1861761 の反応式
Cl.[CH2:2]([CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)C>[CH3:23][O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][N:11]1[CH2:12][CH2:13][CH2:14][CH:9]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10]1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 79557Methyl 5-bromovalerateHCID 161878763-Benzylpiperidine hydrochloride

生成物 1

HCID 543451545-[(3-Benzyl)-1-piperidinyl]valeric acid methyl ester収率 65%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a solution of 3-benzylpiperidine hydrochloride (2 g, 9.4 mmol) in DMF (40 mL) were added methyl 5-bromovalerate (1.6 mL, 11.3 mmol) and potassium carbonate (3.2 g, 23.6 mmol). This heterogeneous mixture was heated at 110° C. for 1 hr then cooled at 25° C., diluted with water (200 mL) and diethyl ether (200 mL). The aqueous solution was extracted with diethyl ether (100 mL) and the collected organic phase was washed with brine (200 mL), dried and concentrated in vacuum. The crude compound was purified by silica gel column chromatography using CH2Cl2/MeOH as eluant to afford the title compound as an oil (1.76 g, 65%). 1H-NMR (CDCl3): 0.8-1.0 (m, 1H); 1.4-1.7 (m, 8H); 1.8-1.95 (m, 2H); 2.25-2.35 (m, 4H); 2.4-2.6 (m, 2H); 2.75-2.9 (m, 2H); 3.65 (8, 3H); 7.132 (d, J=7.0, 2H); 7.186 (d, J=7.2, 11); 7.264 (t, J=7.2, 2H).

後処理

  1. temperaturethen cooled at 25° C.
  2. extractionThe aqueous solution was extracted with diethyl ether (100 mL)
  3. washthe collected organic phase was washed with brine (200 mL)
  4. customdried
  5. concentrationconcentrated in vacuum
  6. customThe crude compound was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a087aad7ddd34ff1abedee2576b04609
出典データセット
uspto-grants-2003_03
特許番号
US06534522B2

反応ノート

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