Diisopropylethylamine → HCID 67500566, compound

HRID 73565Notes

Reaction equation

HRID 73565 reaction equation
[Cl:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[NH:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12].Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].CCN(C(C)C)C(C)C>C(O)(C)C>[Cl:1][CH:2]1[CH2:7][CH2:6][N:5]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[CH2:4][CH:3]1[NH:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27357814-Chloro-3-nitropyridineHCID 67500859Diethyl 4-chloropiperidin-3-ylphosphoramidate

Product 1

HCID 67500566HCID 67500566, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of diethyl 4-chloropiperidin-3-ylphosphoramidate (1.0 equiv.) in isopropyl alcohol (0.1M) was added 4-chloro-3-nitropyridine (2.0 equiv.) and DIEA (1.1 equiv.). The reaction was heated to 70° C. for 18 h, then quenched with water and extracted with ethyl acetate. The organics were dried and concentrated under vacuo. The crude was purified via ISCO (ethyl acetate and hexanes then 10% methanol in DCM) to yield diethyl 4-chloro-1-(3-nitropyridin-4-yl)piperidin-3-ylphosphoramidate in 69% yield. LCMS (m/z): 393.1 (MH+), Rt=2.01 min.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organics were dried
  4. concentrationconcentrated under vacuo
  5. customThe crude was purified via ISCO (ethyl acetate and hexanes

Sources & evidence

ORD record
ord-396d9e8c2cf84064a9f12615fed9f7ee
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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