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Water → (4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methylamine

HRID 272952
ノート
印刷プレビュー

反応式

HRID 272952 の反応式
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([C:23]#[N:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C(OCC)C.CO.ClCCl>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([CH2:23][NH2:24])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 115008424-[4-(1-Isopropylpiperidin-4-yloxy)phenyl]tetrahydropyran-4-carbonitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 68576458(4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methylamine収率 102.2%

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
HCID 3283Diethyl Ether溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution 4-[4-(1-isopropylpiperidin-4-yloxy)phenyl]tetrahydropyran-4-carbonitrile (2.5 g, 7.62 mmol) in dry diethyl ether (15 ml) at 0° C. was added dropwise a solution of LiAlH4 (1.0M solution in Et2O, 22.87 ml, 22.9 mmol). Reaction stirred at 0° C. for 30 min, then warmed up to ambient temperature overnight under a nitrogen atmosphere until complete. The reaction was cooled to 0° C., water (0.9 ml) was added dropwise followed by sodium hydroxide (2.0M, 0.9 ml) and water (2.7 ml). Dichloromethane (25 ml) and methanol (1 ml) were added and the mixture filtered through a short pad of arbocel, eluting with 2% methanol in dichloromethane (200 ml). The organic washings were dried over Na2SO4 and concentrated in vacuo to give the title compound as an orange oil (2.59 g, 100%).

後処理

  1. customReaction
  2. temperaturewarmed up to ambient temperature overnight under a nitrogen atmosphere until complete
  3. temperatureThe reaction was cooled to 0° C.
  4. filtrationthe mixture filtered through a short pad of arbocel
  5. washeluting with 2% methanol in dichloromethane (200 ml)
  6. dry with materialThe organic washings were dried over Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8112c4305d5b4f2d940ba43ab719bb31
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07456164B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート