Hydrochloric Acid → N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-3-ethoxybenzamide hydrochloride

HRID 496873Notes

Reaction equation

HRID 496873 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH2:21])[CH2:15][CH2:14]1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:50]([O:52][C:53]1[CH:54]=[C:55]([CH:59]=[CH:60][CH:61]=1)[C:56](O)=[O:57])[CH3:51].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+].Cl>CN(C=O)C.C(Cl)(Cl)Cl>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[O:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][NH:21][C:56](=[O:57])[C:55]2[CH:59]=[CH:60][CH:61]=[C:53]([O:52][CH2:50][CH3:51])[CH:54]=2)[CH2:17][CH2:18]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 121263-Ethoxybenzoic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733179PyBroPHCID 223224532-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethylamine trifluoroacetate

Product 1

HCID 22322203N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-3-ethoxybenzamide hydrochlorideYield 59.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

The product of Example 1 step (iv) (0.4 g) was dissolved in DMF (10 ml), PyBrop (0.541 g), 3-ethoxybenzoic acid (0.167 g ) and N,N-di-isopropylethylamine (0.5 g) were added. After 18 hours at room temperature chloroform and aqueous NaHCO3 solution were added. The organic phase was separated, dried and concentrated to leave a gum which was purified by chromatography (ethyl acetate:methanol 97:3) to give an oil. Addition of 1.0M ethereal hydrogen chloride solution gave the titled product as a solid (0.14 g).

Workup

  1. customThe organic phase was separated
  2. customdried
  3. concentrationconcentrated
  4. customto leave a gum which
  5. customwas purified by chromatography (ethyl acetate:methanol 97:3)
  6. customto give an oil

Sources & evidence

ORD record
ord-66aaf298fc7646f2b20be9f7cfba311f
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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