Triphenylphosphine → 2-[2-(Piperazin-1-yl)ethoxy]benzonitrile

HRID 1582746Notes

Reaction equation

HRID 1582746 reaction equation
C([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][OH:11])[CH2:5][CH2:4]1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1O)#[N:32].C(OC(N=NC(OCC)=O)=O)C.C1(C)C=CC=CC=1>O1CCCC1>[C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:11][CH2:10][CH2:9][N:6]1[CH2:5][CH2:4][NH:3][CH2:8][CH2:7]1)#[N:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 119072-HydroxybenzonitrileHCID 99422134-(2-Hydroxyethyl)piperazine-1-carbaldehydeHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 227183062-[2-(Piperazin-1-yl)ethoxy]benzonitrileYield 23.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Formyl-4-(2-hydroxyethyl)piperazine (4.95 g) was dissolved in tetrahydrofuran (100 ml), then triphenyl phosphine (10.14 g) and 2-cyanophenol (3.57 g) were added thereto, and 40% azodicarboxylic acid diethyl ester/toluene solution (13.5 ml) was added dropwise thereto, and the title compound (1.60 g) was obtained in the same manner as in Example 47-1).

Sources & evidence

ORD record
ord-5333d02393e34efcbad9222b7174a98c
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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