Acetic Acid → HCID 86649245, compound

HRID 2063928Notes

Reaction equation

HRID 2063928 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])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=O.[Cl-].[F:20][C:21]([F:35])([F:34])[C:22]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:33][CH2:32][NH2+:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1.C(N(CC)CC)C.C(O)(=O)C.C([BH3-])#N>ClC(Cl)C>[O:13]=[C:6]1[N:7]2[C:12]([CH:11]=[CH:10][CH:9]=[CH:8]2)=[C:3]([CH2:1][N:31]2[CH2:32][CH2:33][CH:28]([C:25]3[CH:26]=[CH:27][C:22]([C:21]([F:20])([F:34])[F:35])=[CH:23][CH:24]=3)[CH2:29][CH2:30]2)[CH:4]=[C:5]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 498716Cyano-borohydrideHCID 20634151Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylateHCID 68628594HCID 68628594, compound

Product 1

HCID 86649245HCID 86649245, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

In a 2-5 mL Emrys™ process vial, the ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (599 mg, 2.44 mmol) and the 4-[4-(trifluoromethyl)phenyl]piperidinium chloride (672 mg, 2.53 mmol) were diluted with 4.9 mL of dichloroethane, which was neutralized with the addition of triethylamine (0.41 mL, 2.93 mmol). To the stirring mixture was added glacial acetic acid (0.84 mL, 14.7 mmol) and resin-bound MP-cyanoborohydride (307 mg, 4.89 mmol). The mixture was heated via Emrys Optimizer™ microwave to 120° C. for 20 minutes. After filtration, the filtrate was washed with water (3×20). The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with 30-80% EtOAc in hexanes to provide ethyl 4-oxo-1-({4-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methyl)-4H-quinolizine-3-carboxylate.

Workup

  1. filtrationAfter filtration
  2. washthe filtrate was washed with water (3×20)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography
  7. washeluting with 30-80% EtOAc in hexanes

Sources & evidence

ORD record
ord-bf280b233bfc49029b3624d7b0b33947
Source dataset
uspto-grants-2012_10
Patent number
US08288409B2

Reaction notes

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