Trimethylsilyl iodide → 4-Amino-1-(5-cyano-2-pyridyl)-4-methylpiperidine

HRID 475356Notes

Reaction equation

HRID 475356 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.C[Si](I)(C)C>C(#N)C>[NH2:10][C:11]1([CH3:25])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66756595(5'-Cyano-4-methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-yl)-carbamic Acid Benzyl Ester

Product 1

HCID 129691214-Amino-1-(5-cyano-2-pyridyl)-4-methylpiperidineYield 74.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (5′-cyano-4-methyl-3,4,5,6-tetrahydro-2H-(1,2′)bipyridinyl-4-yl)-carbamic acid benzyl ester (93 mg) and trimethylsilyliodide (62 μL) in acetonitrile (1.5 mL) was heated to 45° C. for 20 minutes. The reaction mixture was cooled and concentrated under reduced pressure. The crude reaction mixture was purified by chromatography (silica gel, eluting with a gradient of 2% MeOH/CH2Cl2/0.1% NH4OH to 6% MeOH/CH2Cl2/0.1% NH4OH) to provide the titled compound (43 mg) as a yellow foam. MS (CI) m/z 217 (M+1)+; 1H NMR (300 MHz, DMSO) δ ppm 8.44 (s, 1H), 7.77 (d, 1H), 6.91 (d, 1H), 3.86-3.78 (m, 2H), 3.59-3.55 (m, 2H), 1.48-1.38 (m, 4H), 1.08 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe crude reaction mixture
  4. customwas purified by chromatography (silica gel
  5. washeluting with a gradient of 2% MeOH/CH2Cl2/0.1% NH4OH to 6% MeOH/CH2Cl2/0.1% NH4OH)

Sources & evidence

ORD record
ord-5003b6a9acbb47b2bbcb6c0ef7a1382d
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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