Triphenylphosphine → Ammonia

HRID 2305601Notes

Reaction equation

HRID 2305601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([OH:17])[CH:16]=1)[C:5]([N:7]([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[O:6].[N:18]1[CH:23]=[CH:22][C:21]([NH:24][CH:25]([CH2:28][CH3:29])[CH2:26]O)=[CH:20][CH:19]=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>C1(C)C=CC=CC=1>[NH3:7].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:17][CH2:26][CH:25]([NH:24][C:21]2[CH:20]=[CH:19][N:18]=[CH:23][CH:22]=2)[CH2:28][CH3:29])[CH:16]=1)[C:5]([N:7]([CH:8]([CH3:9])[CH3:10])[CH:11]([CH3:12])[CH3:13])=[O:6]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 121143182-(Pyridin-4-yl-amino)-butan-1-olHCID 121143203-Chloro-5-hydroxy-N,N-diisopropyl-benzamide

Product 2

HCID 222AmmoniaHCID 18756382HCID 18756382, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-chloro-5-hydroxy-N,N-diisopropyl-benzamide (0.05 g), 2-(pyridin-4-yl-amino)-butan-1-ol (0.023 g), triphenylphosphine (0.04 g) and toluene (1 ml), was treated with diisopropyl azodicarboxylate (0.03 ml) and the resultant solution stirred under nitrogen for 8 days. The reaction mixture was concentrated under reduced pressure and the residue purified by flash column chromatography, eluting with chloroform:methanol:aqueous ammonia (90:10:1) to give an impure sample of the title compound. This impure sample was subjected to preparative H.p.l.c. (system A) and the purified material was treated with 1M hydrogen chloride in diethyl ether to give the title compound as a gum (0.002 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by flash column chromatography
  3. washeluting with chloroform

Sources & evidence

ORD record
ord-e7e82fe4a95f4f34a713e15b4dd83122
Source dataset
uspto-grants-2002_08
Patent number
US06441008B1

Reaction notes

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