4-Cyanobenzaldehyde → N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamine

HRID 983625

반응식

HRID 983625 반응식
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:10]1[C:11]2[CH:2]([NH:1][CH2:18][C:17]3[CH:20]=[CH:21][C:14]([C:12]#[N:13])=[CH:15][CH:16]=3)[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 660424-CyanobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 113555648-Amino-5,6,7,8-tetrahydroquinoline

생성물 1

HCID 22018532N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamine수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 8-amino-5,6,7,8-tetrahydroquinoline (24.3 g, 164 mmol) in dichloromethane (600 mL), at room temperature, was added 4-cyanobenzaldehyde (21.5 g, 164 mmol) and sodium triacetoxyborohydride (45 g, 210 mmol). After 42 hours, the reaction was quenched with 1N NaOH (250 mL). The phases were separated and the organic phase was washed once with brine (200 mL), dried (Na2SO4), and concentrated. Purification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2) provided 30.9 g (72%) of N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamine as a pale yellow solid.

후처리

  1. customthe reaction was quenched with 1N NaOH (250 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed once with brine (200 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

출처 및 근거

ORD 기록
ord-d22da6e769044db88481434a2f7a55ee
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06864265B2

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