Water → 1-benzyl-N,4-dimethylpiperidin-3-amine

HRID 1853377

반응식

HRID 1853377 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([NH:21][C:22](=O)OC)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([NH:21][CH3:22])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 53396489Methyl 1-benzyl-4-methylpiperidin-3-yl-carbamate

생성물 1

HCID 99438891-benzyl-N,4-dimethylpiperidin-3-amine수율 75.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

At about 0° C., lithium aluminum hydride (3.6 g, 92.8 mmol, 5.00 equiv.) was added in several batches to a solution of methyl 1-benzyl-4-methylpiperidin-3-yl-carbamate (5.0 g, 18.1 mmol, 1.00 equiv.) in tetrahydrofuran (100 mL). The resulting solution was heated at reflux for about 16 hours, and then water (10 mL) was added. The mixture was filtered, and the resulting filtrate was concentrated in vacuo to give a crude residue that was then purified by silica gel column chromatography (dichloromethane/methanol (20:1)) to afford the title product as a yellow oil (3.0 g; yield=72%). 1H NMR (300 MHz, CDCl3) δ: 7.20-7.38 (m, 5H), 3.58 (d, J=13.2 Hz, 1H), 3.48 (d, J=13.2 Hz, 1H), 2.60-2.82 (m, 2H), 2.46 (br s, 1H), 2.34 (s, 3H), 2.02-2.22 (m, 2H), 2.64-2.84 (m, 2H), 1.45-1.58 (m, 2H), 0.97 (d, J=6.9 Hz, 3H). LC-MS: m/z=219 (M+H)+.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for about 16 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe resulting filtrate was concentrated in vacuo
  5. customto give a crude residue that
  6. customwas then purified by silica gel column chromatography (dichloromethane/methanol (20:1))

출처 및 근거

ORD 기록
ord-cc0c8a215b0b4ea2b3b55e37661b2238
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962638B2

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