Potassium Carbonate → N-{1-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzenecarboxamide

HRID 876310Notes

Reaction equation

HRID 876310 reaction equation
[C:1]1([C:7]([NH:9][CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:27](OC3C=CC([N+]([O-])=O)=CC=3)=[O:28])[CH2:11]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:39]1[CH2:44][CH2:43][CH:42]([C:45]#[N:46])[CH2:41][CH2:40]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:45]([CH:42]1[CH2:43][CH2:44][N:39]([C:27]([N:12]2[CH2:13][CH:14]([C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([F:24])([F:26])[F:25])=[CH:20][CH:21]=3)[CH2:15][CH:10]([NH:9][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:8])[CH2:11]2)=[O:28])[CH2:40][CH2:41]1)#[N:46]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1382234-CyanopiperidineHCID 667012994-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxylate

Product 1

HCID 66761456N-{1-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

115 mg (0.22 mmol) of 4-nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxylate were initially charged in 3 ml of DMF, and 72 mg (0.65 mmol) of piperidine-4-carbonitrile and 30 mg (0.22 mmol) of potassium carbonate were added. The mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 30 min. The crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 53 mg (48% of theory)

Workup

  1. customThe mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 30 min
  2. customThe crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-9066e38b6aac43ae9c7d5d772e5ef725
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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