Formaldehyde → HCID 68874400, compound

HRID 1435974Notes

Reaction equation

HRID 1435974 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([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)[CH2:3][CH2:2]1.C=O.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.CN(C)C=O>[CH3:21][N:1]1[CH2:6][CH2:5][CH:4]([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)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 50942210HCID 50942210, compound

Product 1

HCID 68874400HCID 68874400, compoundYield 52.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Three drops of glacial acetic acid was added to a solution of 6-(piperidin-4-yloxy)-isoquinolin-1-ylamine (35 mg, 0.14 mmol) in N, N-dimethylformamide (1 ml), followed by addition of formaldehyde (37% aqueous solution, 200 mL). Sodium triacetoxyboro-hydride (150 mg) was added to the mixture, which was shaken for 72 h. Saturated aqueous sodium hydrogen carbonate was added and then the mixture acidified with acetic acid. The mixture was loaded onto a pre-acidified SCX column, washed with methanol and then eluted with 2M ammonia in methanol. The crude product was isolated and further purified using prep-HPLC to give 6-(1-methylpiperidin-4-yloxy)-isoquinolin-1-ylamine (19 mg), EIMS: m/z=258.5 [M+H]+

Workup

  1. washwashed with methanol
  2. washeluted with 2M ammonia in methanol
  3. customThe crude product was isolated
  4. customfurther purified

Sources & evidence

ORD record
ord-e970ddae96fc41c3814712c3db4ad3a5
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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