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

HRID 747340

Reaction equation

HRID 747340 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-bc49d1524049415289a652d0e103bd90
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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