Triphenylphosphine → HCID 57434763, compound

HRID 2420978Notes

Reaction equation

HRID 2420978 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH2:4][CH2:3]1.O[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 133943-CyanophenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 230339654-(1-Methyl-piperidin-4-yl)-butan-1-ol

Product 1

HCID 57434763HCID 57434763, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 4-(1-methyl-piperidin-4-yl)-butan-1-ol (0.74 g, 4.37 mmol), 3-hydroxy-benzonitrile (0.52 g, 4.37 mmol), and 3 mmol/g polymer supported PPh3 (2.30 g, 8.73 mmol) in THF (40 mL) was added diisopropyl azodicarboxylate (1.72 mL, 8.73 mmol) dropwise. After 6 h the mixture was filtered and concentrated. Purification by Method 1 afforded 840 mg (71%) of a yellow oil. MS (ESI): mass calcd for C17H24N2O, 272.19; m/z found, 273.4 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.38-7.33 (m, 1H), 7.24-7.20 (m, 1H), 7.14-7.09 (m, 2H), 3.96 (t, J=6.4, 2H), 2.88-2.80 (m, 2H), 2.26 (s, 3H), 1.94-1.84 (m, 2H), 1.82-1.73 (m, 2H), 1.72-1.64 (m, 2H), 1.52-1.42 (m, 2H), 1.34-1.17 (m, 5H).

Workup

  1. customTo a 0° C.
  2. filtrationAfter 6 h the mixture was filtered
  3. concentrationconcentrated
  4. customPurification by Method 1

Sources & evidence

ORD record
ord-d51469fd9d3c4bdf8c6b8d77fd304d21
Source dataset
uspto-grants-2011_06
Patent number
US07956066B2

Reaction notes

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