Acetic Acid → HCID 68875984, compound

HRID 1436019Notes

Reaction equation

HRID 1436019 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].[NH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[C:28](=[O:32])[NH:27][CH:26]=[CH:25]3)[CH2:16]1.C(O)(=O)C.C(=O)C>CN(C)C=O>[CH2:1]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[C:28](=[O:32])[NH:27][CH:26]=[CH:25]3)[CH2:16]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 44128639HCID 44128639, compound

Product 1

HCID 68875984HCID 68875984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium triacetoxyborohydride (45 mg, 1.8 mol) was added to a solution of 6-(piperidin-3-yloxy)-2H-isoquinolin-1-one (30 mg, 0.12 mmol), acetic acid (100 μl) and acetaldehyde (50 μl or 50 mg) in N, N-dimethylformamide (500 μl) and shaken for 17 hours. The reaction was quenched with water and methanol and passed down an SCX cartridge. The product was purified by preparative HPLC under basic conditions. The clean products were isolated by evaporation under reduced pressure to give 6-(1-ethyl-piperidin-3-yloxy)-2H-isoquinolin-1-one: El-MS: m/z=273.5[M+H]+.

Workup

  1. customThe reaction was quenched with water and methanol
  2. customThe product was purified by preparative HPLC under basic conditions
  3. customThe clean products were isolated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4e9a67f5ce11471491acea1b764fb266
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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