Acetic Acid → HCID 86645054, compound

HRID 407179Notes

Reaction equation

HRID 407179 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])N2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=O.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1([C:31]#[N:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[C:33](O)(=O)C.ClC(Cl)C.C([BH3-])#N>>[C:31]([C:25]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)[CH2:26][CH2:27][N:28]([CH2:1][C:3]2[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[CH:33]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH2:29][CH2:30]1)#[N:32]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 498716Cyano-borohydrideHCID 20634151Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylateHCID 533632714-(Pyridin-2-yl)piperidine-4-carbonitrile

Product 1

HCID 86645054HCID 86645054, compound

Conditions

Temperature
120 °C

Procedure

In a 10-20 mL Emrys™ process vial, a mixture of the ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (684 mg, 2.79 mmol), 4-pyridin-2-ylpiperidine-4-carbonitrile (627 mg, 3.35 mmol), glacial acetic acid (0.96 mL, 16.7 mmol) and 4.1 mL of dichloroethane was stirred vigorously. To the stirring mixture was added resin-bound MP-cyanoborohydride (2.74 g, 5.58 mmol). The mixture was heated via Emrys Optimizer™ microwave to 120° C. for 30 minutes. Filtration and solvent removal provided material, which was subjected to silica gel chromatography eluting with 55-75% ethyl acetate in hexanes to provide ethyl 4-[(4-cyano-4-pyridin-2-ylpiperidin-1-yl)methyl]-1-oxo-1,8a-dihydronaphthalene-2-carboxylate.

Workup

  1. filtrationFiltration and solvent removal
  2. customprovided material, which
  3. washeluting with 55-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c9e61c50e5f341c5a0e351db92514d6e
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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