Potassium Carbonate → HCID 66857098, compound

HRID 2037552Notes

Reaction equation

HRID 2037552 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7].[F:16][C:17]1[CH:18]=[C:19]([C@@H:23]([NH2:25])[CH3:24])[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]([OH:8])([CH2:5][CH:6]=[CH2:7])[CH2:3][CH2:2][NH:25][C@H:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[CH:18]=2)[CH3:24])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7127576(S)-1-(3-fluorophenyl)ethanamineHCID 534729381-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

Product 1

HCID 66857098HCID 66857098, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (547 mg, 2.4 mmol), (S)-1-(3-fluorophenyl)ethanamine (500 mg, 3.6 mmol), K2CO3 (662 mg, 4.8 mmol), and KI (797 mg, 4.8 mmol) in anhydrous CH3CN (15 mL) was stirred at rt under N2. Then the solution was refluxed overnight. The solid was filtered off, and the solvent was removed under reduced pressure. The residue was purified by preparative TLC to afford 3-(4-fluorophenyl)-1-((S)-1-(3-fluorophenyl)ethylamino)hex-5-en-3-ol (350 mg, 44%).

Workup

  1. temperatureThen the solution was refluxed overnight
  2. filtrationThe solid was filtered off
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-89078668d1ff46818091f845e4e84233
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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