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Water → N-Cyclopropyl-4-oxazol-5-yl-N-[1-(3,3,3-trifluoro-propyl)-piperidin-4-yl]-benzamide

HRID 1424539
Notes
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Reaction equation

HRID 1424539 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21](CC(O)(C)C)[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.I[CH2:30][CH2:31][C:32]([F:35])([F:34])[F:33].C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:30][CH2:31][C:32]([F:35])([F:34])[F:33])[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:7]=[CH:8][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:10][CH:11]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 1561651,1,1-Trifluoro-3-iodopropane2×HCID 86709612N-Cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

Product 1

HCID 73053285N-Cyclopropyl-4-oxazol-5-yl-N-[1-(3,3,3-trifluoro-propyl)-piperidin-4-yl]-benzamide

Reagents, catalysts & solvents

1
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of N-cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide (80 mg), 1-iodo-3,3,3-trifluoropropane (108 mg), and K2CO3 (63 mg) in N-methyl-2-pyrrolidone (2 mL) is stirred at room temperature for 4 h and then at 60° C. over night. Since conversion of starting material is still incomplete, K2CO3 (63 mg) and two portions of 1-iodo-3,3,3-trifluoropropane (54 mg each) are added while stirring the reaction mixture for two more days at 80° C. Water is added to the reaction mixture and the aqueous phase is extracted with ethyl acetate. The combined extracts are washed with brine dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 75:25→50:50). The crude product is triturated with diethyl ether, filtered off, and dried to give the title compound. LC (method 3): tR=1.08 min; Mass spectrum (ESI+): m/z=408 [M+H]+.

Workup

  1. waitat 60° C. over night
  2. stirringwhile stirring the reaction mixture for two more days at 80° C
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 75:25→50:50)
  8. customThe crude product is triturated with diethyl ether
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-72727667cb7944d2b81d083c7f7ccb4e
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes