Water → 1-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine

HRID 374464노트

반응식

HRID 374464 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([C:21](OCC)=[O:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([CH2:21][OH:22])[CH2:17][CH2:16]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 18997143HCID 18997143, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 189971411-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of 0.51 g (13.4 mmol) of lithium aluminum hydride in 20 mL of THF under nitrogen was added dropwise a solution of 3.70 g (13.4 mmol) of 1-(2-phenylethyl)-4-methyl-4-carboethoxypiperidine in 15 mL of THF. The solution was heated at reflux for 3 hours. To the cooled reaction mixture (ice bath) was slowly added 0.5 mL of water, followed by 0.5 mL of 15% sodium hydroxide followed by 1.5 mL of water. The precipitated lithium salts were removed by filtration. The filtrate was evaporated to dryness. The residue was reconstituted in methylene chloride, washed with a small amount of water, dried and evaporated to afford 2.97 g of 1-(2-phenylethyl)-4-methyl-4-hydroxymethyl-piperidine as a yellow oil. NMR (CDCl3) δ7.16-7.23 (m, 5H); 3.40 (s, 2H); 2.79-2.87 (m, 2H); 2.57-2.71 (m, 4H); 2.31-2.42 (m, 2H); 1.57-1.63 (m, 5H); 0.97 (s, 3H).

후처리

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 hours
  3. customTo the cooled reaction mixture (ice bath)
  4. customThe precipitated lithium salts were removed by filtration
  5. customThe filtrate was evaporated to dryness
  6. washwashed with a small amount of water
  7. customdried
  8. customevaporated

출처 및 근거

ORD 기록
ord-9d0c5baae47440b693588d284c4ececf
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480892

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