Hydrochloric Acid → HCID 86611333, compound

HRID 2108549Notes

Reaction equation

HRID 2108549 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH:6]([CH3:17])[CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH2:28](Br)[CH:29]=[CH2:30].Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:30]([N:5]([CH:6]([CH3:17])[CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])[C:3](=[O:4])[C:2]([F:1])([F:18])[F:19])[CH:29]=[CH2:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 86590367N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine

Product 1

HCID 86611333HCID 86611333, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A solution of N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine (6.09 g, 15.7 mmol) in toluene (450 mL) was treated with K2CO3 (2.82 g, 20.4 mmol), KOH (2.45 g, 47.1 mmol), n-Bu4NBr (0.506 g, 1.57 mmol) and allyl bromide (2.47 g, 20.4 mmol), and stirred overnight at 80 C. The product mixture was acidified with 10% aqueous HCl, separated, the aqueous phase extracted with ether (500 mL), the combined organic phases were washed with brine (200 mL), dried with Na2SO4 ari concentrated to give 4.45 g of a brown oil.

Workup

  1. customseparated
  2. extractionthe aqueous phase extracted with ether (500 mL)
  3. washthe combined organic phases were washed with brine (200 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationari concentrated

Sources & evidence

ORD record
ord-c525f779f3604b65b06437294fbfb9fc
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

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