Piperidine → Diethyl 2-amino-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3,5-pyridinedicarboxylate

HRID 1766350Notes

Reaction equation

HRID 1766350 reaction equation
C([CH2:3][CH2:4][O:5][C:6](=[O:8])C)#N.[C:9]([C:11]1[CH:18]=CC(C=O)=[CH:13][CH:12]=1)#[N:10].[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[CH2:25]([O:27][C:28](=[O:43])[CH:29]=[C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=1)[CH3:31])[CH3:26]>C(O)C>[NH2:19][C:24]1[N:32]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:42])[F:41])[CH:34]=2)[C:30]([CH3:31])=[C:29]([C:28]([O:27][CH2:25][CH3:26])=[O:43])[CH:22]([C:21]2[CH:13]=[CH:12][C:11]([C:9]#[N:10])=[CH:18][CH:20]=2)[C:23]=1[C:6]([O:5][CH2:4][CH3:3])=[O:8]

Participants

6

Reactant 4

HCID 8082Piperidine2×HCID 660424-CyanobenzaldehydeHCID 2192242-Cyanoethyl acetateHCID 68427624Ethyl-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

Product 1

HCID 10345841Diethyl 2-amino-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Cyanoethylacetate (2.07 g, 18.3 mmol) and 4-cyanobenzaldehyde (2.40 g, 18.3 mmol) are dissolved in ethanol (125 ml) under an argon atmosphere. Piperidine (46.7 mg, 0.55 mmol) is added, and the reaction mixture is stirred for 2 hours at room temperature. An ethanol (300 ml) solution of Example 1A (5.00 g, 18.3 mmol) and additional piperidine (0.156 g, 1.83 mmol) is added, and the reaction mixture is stirred at reflux for 16 hours. The reaction mixture is concentrated in vacuo and chromatographed over silica get with cyclohexane/ethyl acetate mixtures to give a pale yellow oil.

Workup

  1. stirringthe reaction mixture is stirred
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customchromatographed over silica
  5. customget with cyclohexane/ethyl acetate
  6. customto give a pale yellow oil

Sources & evidence

ORD record
ord-ef3ca186367143c385c1a8b9bedf758c
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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