Piperidine-1-propylamine → HCID 11602669, compound

HRID 1158265Notes

Reaction equation

HRID 1158265 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[N:11]([CH3:16])[C:12](Cl)=[N:13][CH:14]=2)[OH:9])[CH:5]=[CH:6][CH:7]=1.[N:17]1([CH2:23][CH2:24][CH2:25][NH2:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(C(C)C)CC)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[N:11]([CH3:16])[C:12]([NH:26][CH2:25][CH2:24][CH2:23][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:13][CH:14]=2)[OH:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 19049Piperidine-1-propylamineHCID 81531DiisopropylethylamineHCID 57597517HCID 57597517, compound

Product 1

HCID 11602669HCID 11602669, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-fluoro-phenyl)-(2-chloro-3-methyl-3H-imidazol-4-yl)-methanol (1 equivalent) in THF (0.2 M) is added 3-piperidin-1-ylpropylamine (1.5 equivalents) and diisopropylethylamine (1.5 equivalents). The mixture is heated at reflux until HPLC analysis shows consumption of the starting material. The reaction mixture is cooled to rt, quenched with satd. aq. NH4Cl, and extracted with EtOAc (2×). The combined organic extracts are washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude material is purified by chromatography or recrystallization to provide the desired product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux until HPLC analysis
  3. customconsumption of the starting material
  4. customquenched with satd
  5. extractionaq. NH4Cl, and extracted with EtOAc (2×)
  6. washThe combined organic extracts are washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material is purified by chromatography or recrystallization

Sources & evidence

ORD record
ord-b3d1da576acc43afaafc48d9d058517a
Source dataset
uspto-grants-2010_10
Patent number
US07807837B2

Reaction notes

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