Ethanol → 4-{3-[4-(3-{4-[Amino(ethoxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide

HRID 644139Notes

Reaction equation

HRID 644139 reaction equation
C(O)C.C(O[C:7](=[NH:37])[C:8]1[CH:36]=[CH:35][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:34]=[CH:33][C:29]([C:30](=[NH:32])[O-:31])=[CH:28][CH:27]=3)[CH2:18][CH2:17]2)=[CH:10][CH:9]=1)C.Cl.[CH2:39]([O:41][NH2:42])[CH3:40].[OH-].[Na+]>O.C(Cl)(Cl)Cl.C(N(CC)CC)C>[NH2:37][C:7](=[N:42][O:41][CH2:39][CH3:40])[C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:34]=[CH:33][C:29]([C:30]([NH2:32])=[O:31])=[CH:28][CH:27]=3)[CH2:18][CH2:17]2)=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 86625839HCID 86625839, compound

Product 1

HCID 866258384-{3-[4-(3-{4-[Amino(ethoxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To an ethanol (8 mL) suspension of 0.20 g of ethyl=4-{3-[4-(3-{4-[ethoxy(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzimidate were sequentially added 0.39 g of O-ethylhydroxylamine hydrochloride and 0.84 mL of triethylamine under cooling with ice, which was then stirred at room temperature for 3.5 days. The reaction mixture was added to a mixture of chloroform and water, which was then adjusted to pH 9.7 using a 20% sodium hydroxide aqueous solution. The organic layer was separated, washed with water, and then dried with anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; chloroform:ethanol=20:1) to provide 0.20 g of 4-{3-[4-(3-{4-[amino(ethoxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=O-ethyloxime as white solid form.

Workup

  1. temperatureunder cooling with ice, which
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-5f5272966c384e8d816670fffc8caef9
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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