Triphenylphosphine → 6-(1-Isopropyl-piperidin-4-yloxy)-quinoline-2-carboxylic acid ethyl ester

HRID 493425Notes

Reaction equation

HRID 493425 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:36]([N:39]1[CH2:44][CH2:43][CH:42](O)[CH2:41][CH2:40]1)([CH3:38])[CH3:37]>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH:42]3[CH2:43][CH2:44][N:39]([CH:36]([CH3:38])[CH3:37])[CH2:40][CH2:41]3)[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 57681568Ethyl 6-hydroxyquinoline-2-carboxylate

Product 1

HCID 576815706-(1-Isopropyl-piperidin-4-yloxy)-quinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 1 g (0.0046 mol) of 6-hydroxy-quinoline-2-carboxylic acid ethyl ester, 2.4 g (0.0092 mol) of triphenylphospine (Fluka), 2.4 g (0.0092 mol) of 1-isopropyl-piperidin-4-ol and 1.6 ml (0.0092 mol) of di-tert.-butyl azadicarboxylate 40% in toluene in 100 ml THF was stirred for a prolonged period of time at 35° C. The mixture was filtered through a pad of silica and washed with 30 ml THF. The mixture was evaporated to dryness and purified on silica eluting with a gradient of DCM/MeOH 98/2. The product fractions were evaporated and the residue was triturated with diethyl ether to yield after drying under vacuum 1.3 mg (83%) of the title compound as white solid. MS (m/e): 343.3 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of silica
  2. washwashed with 30 ml THF
  3. customThe mixture was evaporated to dryness
  4. custompurified on silica eluting with a gradient of DCM/MeOH 98/2
  5. customThe product fractions were evaporated
  6. customthe residue was triturated with diethyl ether
  7. customto yield
  8. dry with materialafter drying under vacuum 1.3 mg (83%) of the title compound as white solid

Sources & evidence

ORD record
ord-6c18ae715d054cf2a288f8d498a16e65
Source dataset
uspto-grants-2009_05
Patent number
US07534891B2

Reaction notes

Loading…