Water → [4-(3-Methoxyphenyl)oxan-4-yl]methanamine

HRID 272809

反応式

HRID 272809 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1.O.[OH-].[Na+]>C(OCC)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:21][NH2:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 187863664-(3-Methoxyphenyl)oxane-4-carbonitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 61264029[4-(3-Methoxyphenyl)oxan-4-yl]methanamine収率 94%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred suspension of LiAlH4 (3.7 g, 96.7 mmol) in diethyl ether (100 mL) cooled at 0° C. was added dropwise a solution of 4-(3-methoxyphenyl)-tetrahydro-pyran-4-carbonitrile (4.2 g, 19.3 mmol) in diethyl ether (100 mL). After being stirred at room temperature for 30 min, the reaction mixture was refluxed for another 15 min. The mixture was cooled to 10° C. and water, sodium hydroxide (15% w/v in water, 0.48 mL) and water again were successively added dropwise. After being stirred for 15 min at room temperature, the mixture was filtered over diatomaceous earth and concentrated. The residue was purified with flash chromatography (DCM/MeOH: 95/5) to provide (4-(3-methoxyphenyl)tetrahydro-pyran-4-yl]methylamine (4 g, 94%).

後処理

  1. temperaturethe reaction mixture was refluxed for another 15 min
  2. temperatureThe mixture was cooled to 10° C.
  3. stirringAfter being stirred for 15 min at room temperature
  4. filtrationthe mixture was filtered over diatomaceous earth
  5. concentrationconcentrated
  6. customThe residue was purified with flash chromatography (DCM/MeOH: 95/5)

出典と根拠

ORDレコード
ord-3409e452878b43d78546b9be2173f632
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

関連ノート

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