4-Iodoaniline → HCID 66790184, compound

HRID 1947266Notes

Reaction equation

HRID 1947266 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=O)[C:4](=O)[CH2:3]1.[I:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.[CH3:24][Si](C#N)(C)C.[OH-:30].[NH4+:31]>CC(O)=O>[C:1]([C:2]1([NH:21][C:20]2[CH:22]=[CH:23][C:17]([I:16])=[CH:18][CH:19]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:30])[CH:4]([CH3:24])[CH2:3]1)#[N:31]

Participants

6

Reactant 4

HCID 108934-IodoanilineHCID 14923Ammonium HydroxideHCID 82115Trimethylsilyl cyanideHCID 14736428HCID 14736428, compound

Product 1

HCID 66790184HCID 66790184, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-methyl-Boc-piperidinone (intermediate I.1.a.1, 863 mg, 4.05 mmol) was dissolved in glacial AcOH (4.05 mL). To the resulting solution was added 4-iodo-aniline (0.886 g, 4.05 mmol) and trimethylsilylcyanide (0.647 mL, 4.86 mmol). The reaction mixture was stirred at rt for 1 h, cooled to 0° C., poured onto 7 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 3:1 cis:trans isomeric mixture. LRMS (M+1-CN)=416.

Workup

  1. temperaturecooled to 0° C.
  2. extractionextracted with DCM twice
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-210d803a08464dd4a7d37f0a1f15b8dd
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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