Hydrochloric Acid → N-[11-(3-fluoro-4-methoxy-phenyl)-11-oxo-undecyl]acetamide

HRID 2306466Notes

Reaction equation

HRID 2306466 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)(=[O:9])[CH3:8].C(NCCCCCCCCCCC(Cl)=O)(=O)C.[F:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[O:48][CH3:49].[Cl-].[Al+3].[Cl-].[Cl-].Cl>CN(C=O)C.C(Cl)Cl.O>[F:41][C:42]1[CH:47]=[C:46]([C:21](=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:7](=[O:9])[CH3:8])[CH:45]=[CH:44][C:43]=1[O:48][CH3:49]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 675762-FluoroanisoleHCID 45408511-Acetamidoundecanoic acidHCID 6451240Aluminum(III) ChlorideHCID 1843429211-Acetylamino-undecanoyl chloride

Product 1

HCID 18434110N-[11-(3-fluoro-4-methoxy-phenyl)-11-oxo-undecyl]acetamideYield 107.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.5 ml of oxalyl chloride is added to a solution of 1.2 g of 11-acetylamino-undecanoic acid and 5 drops of DMF in 15 ml of methylene chloride at 0° C. and the mixture is stirred at RT for 3 hrs. The solution of the 11-acetylamino-undecanoyl chloride is treated under argon with 0.6 g of 2-fluoroanisole, cooled to −15° C. and treated with 1.4 g of aluminium chloride. After 2 hrs. at −15° C. the mixture is left to warm to room temperature overnight. The solution is treated with 15 ml of 1M hydrochloric acid at 0° C. and then with 20 ml of water. The organic phase is separated and washed with 1M hydrochloric acid, with water and with saturated sodium bicarbonate solution, dried and concentrated. 1.8 g of N-[11-(3-fluoro-4-methoxy-phenyl)-11-oxo-undecyl]acetamide are obtained.

Workup

  1. temperaturecooled to −15° C.
  2. waitAfter 2 hrs
  3. waitat −15° C. the mixture is left
  4. temperatureto warm to room temperature overnight
  5. customThe organic phase is separated
  6. washwashed with 1M hydrochloric acid, with water and with saturated sodium bicarbonate solution
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-84ac9039dd8d4cddb08ba3c2cbfb5fac
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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