Triphenylphosphine → 4-(3-((4-Chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholine

HRID 489134Notes

Reaction equation

HRID 489134 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.O[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 1995763-Morpholino-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1355837314-Chloro-6-methoxyquinolin-7-ol

Product 1

HCID 222652574-(3-((4-Chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholineYield 69.3%

Procedure

A mixture of 4-chloro-6-methoxy-7-hydroxy quinoline (0.63 g, 3.0 mmol) and N(3-hydroxypropyl)morpholine (0.54 g, 3.8 mmol) was treated with diethyl azodicarboxylate (1.38 g, 6.0 mmol) and triphenylphosphine (1.57 g, 6.0 mmol) at room temperature for 2 hours. Purification by flash chromatography on silica gel, eluting with 0-20% methanol in 1:1 ethyl acetate/dichloromethane yielded 4-Chloro-6-methoxy-7-(3-morpholinopropoxy)-quinoline (0.70 g, 69% yield) as white solid:

Workup

  1. customPurification by flash chromatography on silica gel
  2. washeluting with 0-20% methanol in 1:1 ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-8c78d947ed234de09b16d3f4f114658d
Source dataset
uspto-grants-2005_12
Patent number
US06977259B2

Reaction notes

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