Iodoacetamide → HCID 66712037, compound

HRID 1262426Notes

Reaction equation

HRID 1262426 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O.I[CH2:37][C:38]([NH2:40])=[O:39]>C(#N)C>[C:16]([C:10]1([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14][N:13]([CH2:37][C:38]([NH2:40])=[O:39])[CH2:12][CH2:11]1)#[N:17]

Participants

5

Reactant 3

HCID 3727Iodoacetamide2×HCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)2×HCID 574160994-(4-Nitrophenyl)piperidine-4-carbonitrile

Product 1

HCID 66712037HCID 66712037, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-(4-Nitro-phenyl)-piperidine-4-carbonitrile (0.795 g, 3.44 mmol) and MP-Carbonate resin (3.16 mmol/g loading; 2.18 g, 6.88 mmol) were combined in Acetonitrile (24.0 mL) and Iodoacetamide (0.720 g, 3.70 mmol) was then added and then stirred overnight. After 24 h, conversion was not complete, so additional MP-Carbonate resin (1.21 g, 3.82 mmol), Iodoacetamide (0.405 g, 2.08 mmol) and Acetonitrile (30.0 mL, 574 mmol) were added. After 8 h, the reaction was complete. Solubilize the precipitated product with DCM:MeOH, filter off resin and wash with DCM:MeOH. Conc. onto 10 g silica gel. ISCO (40 g, 0-20% MeOH:EtOAc) to afford 2-[4-Cyano-4-(4-nitro-phenyl)-piperidin-1-yl]-acetamide (1.09 g; Yield=100) as a white solid. 1H-NMR (DMSO-d6): 8.31 (d, 2H, J=8.7 Hz), 7.87 (d, 2H, J=8.7 Hz), 7.35 (br s, 1H), 7.18 (br s, 1H), 2.97 (m, 4H), 2.50 (m, 2H), 2.22 (m, 2H), 2.13 (m, 2H).

Workup

  1. waitAfter 24 h
  2. waitAfter 8 h
  3. filtrationSolubilize the precipitated product with DCM:MeOH, filter off resin
  4. washwash with DCM

Sources & evidence

ORD record
ord-83581aa235294052927fa06bc2691547
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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