Triphenylphosphine → HCID 86624203, compound

HRID 657596Notes

Reaction equation

HRID 657596 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:17])=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1.O[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:17])=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 714237102-[1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl]ethan-1-ol

Product 1

HCID 86624203HCID 86624203, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 50 mL dry three-necked flask, 0.554 g (0.002 mol) of self-made 2-[1-(3,6-dichloro-pyridazin-4-yl)-piperidin-4-yl]-ethanol, 0.20 g (0.002 mol) of p-hydroxybenzonitrile, 0.612 g of triphenylphosphine were added, 15 mL of anhydrous tetrahydrofuran was added under conditions of ice bath and nitrogen gas protection, then 0.35 mL of diethyl azodiformate (DEAD) dissolved in 5 mL of anhydrous tetrahydrofuran, was added dropwise into the flask. After the dropwise addition, the temperature was elevated to room temperature, the agitation was kept overnight. On the next day, the solvent was removed by evaporation using a rotation evaporator, the residue was poured into 100 mL of water, extracted for three times by using total 150 mL of dichloromethane, the extract solutions were combined together, dried over anhydrous Na2SO4, concentrated, and separated by column chromatograph (eluent, petroleum ether:ethyl acetate:methanol=10:3:0.1) to obtain 0.26 g of 4-{2-[1-(3,6-dichloro-pyridazin-4-yl)-piperidin-4-yl]-ethoxy}-benzonitrile, a white solid. Yield: 34.0%, m.p. 138˜139° C. 1HNMR (400MHz, CDCl3) δppm: 1.49˜1.55(m, 2H), 1.83˜1.86(m, 3H), 1.91˜1.94(dbrs, 2H), 2.82˜2.87(dt, 2H, J=11.4Hz), 3.76˜3.79(dbrs, 2H), 4.08˜4.11(t, 2H, J=5.8Hz), 6.85(s, 1H), 6.94˜6.96(d, 2H, J=8.8Hz), 7.58˜7.61(d, 2H, J=8.8Hz), 7.40(s, 1H).

Workup

  1. additionwas added dropwise into the flask
  2. additionAfter the dropwise addition
  3. customwas elevated to room temperature
  4. customOn the next day, the solvent was removed by evaporation
  5. customa rotation evaporator
  6. additionthe residue was poured into 100 mL of water
  7. extractionextracted for three times
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated
  10. customseparated by column chromatograph (eluent, petroleum ether:ethyl acetate:methanol=10:3:0.1)

Sources & evidence

ORD record
ord-bac4c040bb214cc588d72bb6c5cd43d7
Source dataset
uspto-grants-2011_12
Patent number
US08076339B2

Reaction notes

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