Nitrogen → 2-(4-(3-(Aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol

HRID 2062264Notes

Reaction equation

HRID 2062264 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([CH3:28])=[CH:25][CH:26]=3)[N:21]=[C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[OH:35])[N:19]=2)[CH2:13]1)C1C=CC=CC=1.N#N>[Pd].CCO.CCOC(C)=O>[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([CH3:28])=[CH:25][CH:26]=3)[N:21]=[C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[OH:35])[N:19]=2)[CH2:13]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 136121399Benzyl(1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate

Product 1

HCID 1361215722-(4-(3-(Aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of benzyl(1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (1.75 g, 3.63 mmol) and EtOH/EtOAc (50 mL/20 mL) was heated to obtain a homogeneous solution. After cooling to room temperature, Pd/C (175 mg, 10% wt Pd on carbon) was added and the flask was sealed with a septum. The same flask was 3 times charged with N2 and evacuated under vacuum. The mixture was then stirred under an H2 atmosphere at ambient pressure for 1 h. The product was collected by filtration through a plug of Celite, eluting with MeOH. The filtrate was concentrated to a yellow solid (1.26 g) to give 2-(4-(3-(aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol. LC/MS: m/z 349.3 (M+H)+ at 1.80 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperaturewas heated
  2. customto obtain a homogeneous solution
  3. customthe flask was sealed with a septum
  4. customevacuated under vacuum
  5. filtrationThe product was collected by filtration through a plug of Celite
  6. washeluting with MeOH
  7. concentrationThe filtrate was concentrated to a yellow solid (1.26 g)

Sources & evidence

ORD record
ord-021c8aed8566487687fc50b3b4a09e20
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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