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

HRID 1597263노트

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HRID 1597263 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 1914081-Benzyl-4-cyano-4-phenylpiperidineHCID 21226445Aluminium lithium hydride

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-178d0cad4cc04375a2a0ab5afd5a7f55
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294537B1

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