Diisopropylethylamine → HCID 59863017, compound

HRID 2064084Notes

Reaction equation

HRID 2064084 reaction equation
Cl.Cl.[O:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.F[C:26]1[CH:31]=[C:30]([O:32][CH2:33][C:34]([F:37])([F:36])[F:35])[CH:29]=[CH:28][C:27]=1[N+:38]([O-:40])=[O:39]>CN(C)C=O>[N+:38]([C:27]1[CH:28]=[CH:29][C:30]([O:32][CH2:33][C:34]([F:35])([F:36])[F:37])=[CH:31][C:26]=1[NH:15][CH:12]1[CH2:13][CH2:14][N:9]([CH:6]2[CH2:5][CH2:4][O:3][CH2:8][CH2:7]2)[CH2:10][CH2:11]1)([O-:40])=[O:39]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 451567511-(Oxan-4-yl)piperidin-4-amine dihydrochlorideHCID 57423924HCID 57423924, compound

Product 1

HCID 59863017HCID 59863017, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A stirred suspension of 1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine dihydrochloride (diHCl salt of D9, 350 mg, 1.4 mmol) in dimethylformamide (6 ml) at room temperature under argon was treated with N,N-diisopropylethylamine 51 mg, 4.0 mmol), then stirred for 10 minutes before adding 2-fluoro-1-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzene (D55, 280 mg, 1.2 mmol) and heating at 75° C. for 36 hrs. The solution was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by chromatography on silica gel (20 g) eluting with 0-20% methanol/ethyl acetate to afford the title compound as a bright yellow solid (210 mg, 45%).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. additionthe residue treated with 10% Na2CO3 solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography on silica gel (20 g)
  8. washeluting with 0-20% methanol/ethyl acetate

Sources & evidence

ORD record
ord-e3c8b9505fa545788ffc5a7f5905880c
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

Loading…