Methanol → HCID 58615400, compound

HRID 853030Notes

Reaction equation

HRID 853030 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].CO>C(#N)C.ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([O:26][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 111737784-Chloro-6-iodoquinoline

Product 1

HCID 58615400HCID 58615400, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 4-chloro-6-iodo-quinoline (217.5 mg, 1 mmol, prepared by similar procedure to example 1e), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 0.75 mmol), and 1-tert-butyl-2,2,4,4-pentakis(dimethylamino)-2λ5, 4λ5-catenadi(phosphazene) in tetrahdyrofuran (2M, 0.75 ml, 1.5 mmol) in acetonitrile (3.5 ml) was stirred at 100° C. for 30 min in microwave instrument (Personal Chemistry). After cooling the reaction, the solvent was evaporated, followed by addition of water, some of sodium carbonate saturated solution. The resulting solution was extracted with dimethylene chloride three times. The combined organic layer was dried over the brain, sodium sulfate, then evaporated to give a reddish gel. Flash chromatography (Merck silica gel 60, 230-400 mesh, 0%-3% methanol in dichloromethane for 30 min) afforded 4-(6-iodo-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (262.5 mg, 77%) as A light yellow solid. LC-MS m/e 455 (MH+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction
  3. customthe solvent was evaporated
  4. additionfollowed by addition of water
  5. extractionThe resulting solution was extracted with dimethylene chloride three times
  6. dry with materialThe combined organic layer was dried over the brain, sodium sulfate
  7. customevaporated
  8. customto give a reddish gel

Sources & evidence

ORD record
ord-abce02589cda40db92dd0df9abc07947
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

Loading…