Water → (1-Benzyl-4-phenylpiperidin-4-yl)methanamine

HRID 1597263ノート

反応式

HRID 1597263 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([C:26]#[N:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[NH2:27][CH2:26][C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:19][N:14]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:15][CH2:16]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 1914081-Benzyl-4-cyano-4-phenylpiperidineHCID 21226445Aluminium lithium hydride

生成物 1

HCID 804238(1-Benzyl-4-phenylpiperidin-4-yl)methanamine収率 54.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of 2.8 g of lithium aluminum hydride in 50 ml of THF is cooled to 0° C. and a solution of 20 g of 1-benzyl-4-cyano-4-phenylpiperidine in 50 ml of THF is added dropwise. The mixture is kept stirring for 1 hour at RT and then heated at 40° C. for 1 hour. The reaction mixture is cooled on an ice bath, and 3 ml of water, 3 ml of a 4N solution of NaOH and 12 ml of water are added successively. The inorganic salts are filtered and the filtrate evaporated under vacuum. The residue is chromatographed on silica H, eluting with the gradient of the DCM/MeOH mixture from (100/3; v/v) to (100/10; v/v). 11 g of the expected product are obtained.

後処理

  1. temperatureheated at 40° C. for 1 hour
  2. temperatureThe reaction mixture is cooled on an ice bath
  3. filtrationThe inorganic salts are filtered
  4. customthe filtrate evaporated under vacuum
  5. customThe residue is chromatographed on silica H
  6. washeluting with the gradient of the DCM/MeOH mixture from (100/3; v/v) to (100/10; v/v)

出典と根拠

ORDレコード
ord-178d0cad4cc04375a2a0ab5afd5a7f55
出典データセット
uspto-grants-2001_09
特許番号
US06294537B1

反応ノート

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