Hydrochloric Acid → N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-N-(3-methoxybenzyl)amine dihydrochloride

HRID 1059025Notes

Reaction equation

HRID 1059025 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.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[CH:45]=O.C([O-])(O)=O.[Na+].[ClH:55]>CN(C=O)C.ClCCCl.C(Cl)(Cl)Cl.C(N(CC)CC)C>[ClH:8].[ClH:55].[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][CH2:45][C:44]2[CH:47]=[CH:48][CH:49]=[C:42]([O:41][CH3:40])[CH:43]=2)[CH2:17][CH2:18]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 115693-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 223224532-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethylamine trifluoroacetate

Product 1

HCID 22322447N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-N-(3-methoxybenzyl)amine dihydrochloride

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of the product of Example 1 step (iv) (0.11 g) in a mixture of DMF (1.5 ml) and 1,2-dichloroethane (3 ml) was stirred under an atmosphere of nitrogen. Sodium triacetoxyborohydride (0.097 g), 3-methoxybenzaldehyde (0.041 g) and triethylamine (0.046 g) were added and the mixture stirred for 18 hours at room temperature. Chloroform and aqueous NaHCO3 solution were added, the organic phase separated, dried and concentrated to a gum. Purification by chromatography (chloroform:triethylamine:methanol, 89:10:1) gave an oil which was treated with 1.0M ethereal hydrogen chloride solution to give the titled product as a solid (0.067 g).

Workup

  1. stirringthe mixture stirred for 18 hours at room temperature
  2. customthe organic phase separated
  3. customdried
  4. concentrationconcentrated to a gum
  5. customPurification by chromatography (chloroform:triethylamine:methanol, 89:10:1)
  6. customgave an oil which

Sources & evidence

ORD record
ord-7cbffd55882749b487fe7257d07aa1c8
Source dataset
uspto-grants-2003_02
Patent number
US06518286B1

Reaction notes

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