Potassium Carbonate → 6-([3-Piperazin-1-yl]-azetidin-1-yl)carbonyl-1,2,3,4-tetrahydroquinoline

HRID 2365620Notes

Reaction equation

HRID 2365620 reaction equation
FC(F)(F)C([N:5]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:14][N:13]([C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH2:22][CH2:21][CH2:20]4)=[O:16])[CH2:12]2)[CH2:7][CH2:6]1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[N:8]1([CH:11]2[CH2:14][N:13]([C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH2:22][CH2:21][CH2:20]4)=[O:16])[CH2:12]2)[CH2:9][CH2:10][NH:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 596257696-({3-[4-(Trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

Product 1

HCID 596259076-([3-Piperazin-1-yl]-azetidin-1-yl)carbonyl-1,2,3,4-tetrahydroquinolineYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 20b (529 mg, 1.33 mmol) in MeOH (10 mL) was added K2CO3 (368 mg, 2.66 mmol). The reaction mixture was stirred at room temperature for 30 min. The resultant mixture was filtered, concentrated under reduced pressure, and the resultant residue was partitioned between CH2Cl2 and H2O. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give compound 20c (370 mg). LC/MS m/z (M+H+) 301.0.

Workup

  1. filtrationThe resultant mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe resultant residue was partitioned between CH2Cl2 and H2O
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f59a91c5a5847f0a3166ff9ea1e6b1a
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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