Ethanol → HCID 86625841, compound

HRID 644140Notes

Reaction equation

HRID 644140 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.[F:39][C:40]([F:45])([F:44])[CH2:41][O:42][NH2:43].C(N(CC)CC)C>O.C(Cl)(Cl)Cl>[NH2:37][C:7](=[N:43][O:42][CH2:41][C:40]([F:45])([F:44])[F:39])[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

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 19853822O-(2,2,2-Trifluoroethyl)hydroxylamine hydrochlorideHCID 86625839HCID 86625839, compound

Product 1

HCID 86625841HCID 86625841, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To an ethanol (6 mL) suspension of 0.20 g of ethyl=4-{3-[4-(3-{4-[ethoxy(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzimidate were added 0.61 g of O-(2,2,2-trifluoroethyl)hydroxylamine hydrochloride and 0.84 mL of triethylamine at room temperature, which was then stirred at the same temperature for one week. Chloroform and water were added to the reaction solution. The organic layer was separated, washed with a saturated sodium chloride aqueous solution, and then dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; chloroform:ethanol=30:1), to which hexane was then added, followed by collecting the solid by filtration to provide 0.12 g of 4-{3-[4-(3-{4-[amino(2,2,2-trifluoroethoxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=O-(2,2,2-trifluoroethyl)oxime as white solid form.

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated sodium chloride aqueous solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe resultant residue was purified
  6. additionto which hexane was then added
  7. customby collecting the solid
  8. filtrationby filtration

Sources & evidence

ORD record
ord-c75d0d292c3f4168894bd30163bf0922
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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