Benzaldehyde → HCID 68875613, compound

HRID 1435987Notes

Reaction equation

HRID 1435987 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[NH2:12])=[CH:4][C:3]=1[O:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(O)(=O)C.CN(C)C=O>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([O:13][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][C:2]=2[CH3:1])[C:9]([NH2:12])=[N:8][CH:7]=[CH:6]3)[CH2:15][CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 68874874HCID 68874874, compound

Product 1

HCID 68875613HCID 68875613, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

A couple of drops of glacial acetic acid was added to a solution of 7-methyl-6-(piperidin-4-yloxy)isoquinolin-1-ylamine (30 mg, 0.117 mmol) in N, N-dimethylformamide (1 ml), followed by addition of benzaldehyde (50 μL). The mixture was then treated with sodium triacetoxyborohydride (100 mg) and stirred for 2 h. Water (1 ml) was added, the mixture was stirred for 30 min and then purified by prep-HPLC to give 6-(1-benzyl-piperidin-4-yloxy)-7-methylisoquinolin-1-ylamine (24 mg), El-MS: m/z=348.3 [M+H]+.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-e0f02ae517dc4ea5940bfc40132f4f43
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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