Ammonium formate → 4-Methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-ylamine

HRID 855827Notes

Reaction equation

HRID 855827 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:23])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)(C)C.[Pd]>[CH3:23][C:11]1([NH2:10])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66756915(4-methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-yl)-carbamic acid benzyl ester

Product 1

HCID 178607674-Methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of (4-methyl-3,4,5,6-tetrahydro-2H-(1,2′)bipyridinyl-4-yl)-carbamic acid benzyl ester (0.06 g, 0.185 mmol) in isopropanol (1.8 mL) at room temperature was added ammonium formate (0.047 g, 0.75 mmol) and 5 mg of 10% Pd/C under nitrogen. The reaction mixture was heated under microwave conditions at 150° C. for 30 minutes, cooled, filtered through Celite and concentrated under reduced pressure to provide the titled compound. MS (CI) m/z 192 (M+1).

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36b0ed82a7364ae2b7b5891138a071ff
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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