4-Iodoaniline → HCID 66791326, compound

HRID 1947262Notes

Reaction equation

HRID 1947262 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[I:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C[Si]([C:27]#[N:28])(C)C.[OH-].[NH4+]>C(#N)C>[C:27]([C:11]1([NH:20][C:19]2[CH:21]=[CH:22][C:16]([I:15])=[CH:17][CH:18]=2)[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1)#[N:28]

Participants

6

Reactant 4

HCID 108934-IodoanilineHCID 14923Ammonium HydroxideHCID 82115Trimethylsilyl cyanideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 66791326HCID 66791326, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Boc-piperidinone (10 g, 50.2 mmol) was dissolved in acetonitrile (50 mL) and concentrated in vacuo twice, dissolved in glacial AcOH (50 mL). To the resulting solution was added 4-iodo-aniline (10.99 g, 50.2 mmol) and trimethylsilylcyanide (8 mL, 60.2 mmol). The reaction mixture was stirred at rt for 1 h, cooled to 0° C., poured onto 50 ml ammonium hydroxide and ice/water, extracted with DCM twice. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the desired product as a purple foam. LRMS (M+1-CN)=401.

Workup

  1. concentrationconcentrated in vacuo twice
  2. dissolutiondissolved in glacial AcOH (50 mL)
  3. temperaturecooled to 0° C.
  4. extractionextracted with DCM twice
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2239352d6f8c4f62804dc8ad29180c26
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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