Benzaldehyde → HCID 68874212, compound

HRID 1435973Notes

Reaction equation

HRID 1435973 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([NH2:18])=[N:13][CH:12]=[CH:11]3)[CH2:2]1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(#N)C>[CH2:19]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([NH2:18])=[N:13][CH:12]=[CH:11]3)[CH2:2]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 688740866-(Piperidin-3-yloxy)isoquinolin-1-ylamine

Product 1

HCID 68874212HCID 68874212, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

A couple of drops of glacial acetic acid was added to a solution of racemic 6-(piperidin-3-yloxy)-isoquinolin-1-ylamine (52 mg, 0.214 mmol) and benzaldehyde (26 mL, 0.256 mmol) in acetonitrile (2 ml). The mixture was stirred for 20 minutes and then sodium triacetoxyborohydride (68 mg, 0.321 mmol) was added in portions. The mixture was stirred at ambient temperature for 20 h then concentrated in vacuo. The mixture was then partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate. The organic layer was separated then concentrated in vacuo to give a residue. The residue was purified by prep-HPLC to give 6-(1-benzylpiperidine-3-yloxy)isoquinolin-1-yl amine (73 mg) El-MS: m/z=334.3 [M+H]+.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 20 h
  2. concentrationthen concentrated in vacuo
  3. customThe mixture was then partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate
  4. customThe organic layer was separated
  5. concentrationthen concentrated in vacuo
  6. customto give a residue
  7. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-d23215e05eb247bfaad9d8dadaba340b
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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