Triphenylphosphine → HCID 57619655, compound

HRID 2240341Notes

Reaction equation

HRID 2240341 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][N:11]1[CH2:16][CH2:15][CH:14](O)[CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 133943-CyanophenolHCID 660484-Piperidinol, 1-methyl-HCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 57619655HCID 57619655, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxy-benzonitrile (500 mg, 4.17 mmol), 1-methyl-piperidin-4-ol (467 mg, 4.17 mmol) and triphenyl phosphine (1.64 g, 6.26 mmol) in tetrahydrofuran (40 mL) was added diisopropyl azodicarboxylate (1.23 μL, 6.26 mmol) dropwise. The reaction mixture was stirred for 4 hr at rt. The solution was concentrated to dryness and the residue was chromatographered using ethyl acetate then ethyl acetate/methanol (8:1) to give the title compound (380 mg, 42%). MS (DCI/NH3) m/z 217 (M+1)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.60 (m, 2H) 1.91 (m, 2H) 2.15 (m, 2H) 2.16 (s, 3H) 2.60 (m, 2H) 4.46 (m, 1H) 7.28 (dd, J=7.67, 1.84 Hz, 1H) 7.35 (d, J=7.36 Hz, 1H) 7.45 (m, 2H).

Workup

  1. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-e2f8f3a6fd724a6a9590674cbee2ef16
Source dataset
uspto-grants-2010_05
Patent number
US07723367B2

Reaction notes

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