Trimethylsilyl iodide → (4-Amino-4-methyl-piperidin-1-yl)-pyridin-4-yl-methanone

HRID 475372Notes

Reaction equation

HRID 475372 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1)C1C=CC=CC=1.I[Si](C)(C)C>C(#N)C>[NH2:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)=[O:18])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66757104(4-Methyl-1-(pyridine-4-carbonyl)-piperidin-4-yl)-carbamic acid benzyl ester

Product 1

HCID 66756836(4-Amino-4-methyl-piperidin-1-yl)-pyridin-4-yl-methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution (4-methyl-1-(pyridine-4-carbonyl)-piperidin-4-yl)-carbamic acid benzyl ester (0.085 g, 0.24 mmol) in acetonitrile (2.0 mL) at room temperature was added iodotrimethysilane (0.06 mL, 0.36 mmol). The reaction mixture was stirred at 50° C. for 30 minutes and concentrated under reduced pressure. The solid residue was washed with acetone and filtered to provide titled compound. MS (CI) m/z 220 (M+1)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 8.89 (d, 2H), 7.74 (d, 2H), 4.04 (m, 2H, NH2), 3.42-3.25 (m, 4H), 1.77-1.45 (m, 4H), 1.42 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe solid residue was washed with acetone
  3. filtrationfiltered

Sources & evidence

ORD record
ord-75b0451ec6854af0b9f6d9ee21e2e140
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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