4-Quinolinecarboxaldehyde → 2-(Quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-amine

HRID 2196588Notes

Reaction equation

HRID 2196588 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2.[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=O)=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][N:6]2[CH2:5][CH2:4][C:3]3[C:2]([NH2:1])=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:7]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 780724-QuinolinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 162174995-Amino-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 597568762-(Quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-amineYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2,3,4-tetrahydro-5-aminoisoquinoline (500 mg, 3.37 mmol) was dissolved in tetrahydrofuran (15 mL) then added 4-quinolinecarboxaldehyde (556 mg, 3.54 mmol) and sodium triacetoxyborohydride (786 mg, 3.71 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was quenched with saturated aqueous sodium bicarbonate then concentrated under vacuum. The remaining residue was dissolved in ethyl acetate then washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude material was purified by silica gel chromatography (50% to 80% ethyl acetate/hexane) to afford 2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-amine (805 mg) as a yellow solid. MS (ESI, pos. ion) m/z: 290.1 (M+1).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  2. concentrationthen concentrated under vacuum
  3. dissolutionThe remaining residue was dissolved in ethyl acetate
  4. washthen washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude material was purified by silica gel chromatography (50% to 80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4ccf79939866450d99febcfe09316d2d
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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