Acetic Acid → HCID 50942209, compound

HRID 1435975Notes

Reaction equation

HRID 1435975 reaction equation
C(O)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([NH2:22])=[N:17][CH:16]=[CH:15]3)[CH2:7][CH2:6]1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.O>[CH2:23]([N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([NH2:22])=[N:17][CH:16]=[CH:15]3)[CH2:7][CH2:6]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 50942210HCID 50942210, compound

Product 1

HCID 50942209HCID 50942209, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A drop of glacial acetic acid was added to a solution of 6-(piperidin-4-yloxy)-isoquinolin-1-ylamine (20 mg, 0.082 mmol) in N, N-dimethylformamide (0.5 ml), followed by addition of benzaldehyde (20 mL). The mixture was then treated with sodium triacetoxyborohydride (50 mg) and shaken for 2 h. Water (0.5 ml) was added, the mixture was stirred overnight and then purified by prep-HPLC to give 6-(1-benzyl-piperidin-4-yloxy)-isoquinolin-1--ylamine (28 mg), El-MS: m/z=334.3 [M+H]+.

Workup

  1. stirringthe mixture was stirred overnight
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-3216bdc1be144c13a4af4735ad538f23
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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