Hydroxyamine hydrochloride → HCID 86746098, compound

HRID 847393Notes

Reaction equation

HRID 847393 reaction equation
C(O)(=O)/C=C\C(O)=O.[C:9]([C:12]1[S:21][C:20]2[CH2:19][CH2:18][CH2:17][N:16]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][N:29]([C:32]4[N:37]=[CH:36][CH:35]=[CH:34][N:33]=4)[CH2:28][CH2:27]3)[C:15](=[O:38])[C:14]=2[CH:13]=1)(=O)[CH3:10].Cl.[OH:40][NH2:41].C(=O)([O-])O.[Na+]>C(O)C>[OH:40][N:41]=[C:9]([C:12]1[S:21][C:20]2[CH2:19][CH2:18][CH2:17][N:16]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][N:29]([C:32]4[N:37]=[CH:36][CH:35]=[CH:34][N:33]=4)[CH2:28][CH2:27]3)[C:15](=[O:38])[C:14]=2[CH:13]=1)[CH3:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 67755601HCID 67755601, compound

Product 1

HCID 86746098HCID 86746098, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6.0 g of 2-acetyl-5,6,7,8-tetrahydro-5-[4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl]-4H-thieno[3,2-c]azepin-4-one maleate in 100 ml of ethanol were added 0.92 g of hydroxyamine hydrochloride and 4.0 g of sodium hydrogencarbonate with stirring and the mixture was refluxed for 5 hours. After cooling, the mixture was concentrated under reduced pressure, to the residue was added water and the solution was extracted with chloroform. The extract was washed with water, dried and concentrated in vacuo. The resulting crystals were recrystallized from a mixed solvent of ethanol and isopropyl ether to give 4.95 g of 5,6,7,8-tetrahydro-2-(1-(hydroxyimino)ethyl)-5-[4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl]-4H-thieno[3,2-c]azepin-4-one as white crystals, melting at 144°-146° C.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure, to the residue
  4. additionwas added water
  5. extractionthe solution was extracted with chloroform
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe resulting crystals were recrystallized from a mixed solvent of ethanol and isopropyl ether

Sources & evidence

ORD record
ord-390a9a693fa44756a249b210a9bc3480
Source dataset
uspto-grants-1992_08
Patent number
US05141930

Reaction notes

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