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

HRID 1853377

反応式

HRID 1853377 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 99438891-benzyl-N,4-dimethylpiperidin-3-amine収率 75.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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))

出典と根拠

ORDレコード
ord-cc0c8a215b0b4ea2b3b55e37661b2238
出典データセット
uspto-grants-2015_02
特許番号
US08962638B2

関連ノート

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