Sodium Hydroxide → HCID 178473766, compound

HRID 249305Notes

Reaction equation

HRID 249305 reaction equation
Br.[C:2]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH:7](Br)[CH2:6]1)(=[O:4])[CH3:3].N[N:14]=[CH:15][NH:16][C:17]([NH2:19])=[S:18].[OH-].[Na+].[OH-].[NH4+:23]>C(O)C.CO.C(Cl)(Cl)Cl>[C:2]([N:5]1[CH2:10][CH2:9][C:8]2[N:19]=[C:17]([NH:16][C:15]([NH2:23])=[NH:14])[S:18][C:7]=2[CH2:6]1)(=[O:4])[CH3:3]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 197611761-Acetyl-3-bromopiperidin-4-one hydrobromideHCID 178514401HCID 178514401, compound

Product 1

HCID 178473766HCID 178473766, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

N-Acetyl-3-bromo-4-piperidone hydrobromide (12.09 g, 40 mmol) was added to a suspension of aminoiminomethylthiourea (4.735 g, 40 mmol) in ethanol (40 ml) at 70°. After completion of the addition, the reaction mixture was allowed to stir at 40° for 48 hours. Addition of sodium hydroxide (1.6 g, 40 mmol) was followed by stirring at 40° for an additional 72 hours. Removal of solvent gave a crude oil which was subjected to column chromatography (eluant: 89:10:1 of chloroform:methanol:concentrated ammonium hydroxide) to provide the title product (822 mg, 3.4 mmol, 9% yield).

Workup

  1. additionAfter completion of the addition
  2. stirringby stirring at 40° for an additional 72 hours
  3. customRemoval of solvent
  4. customgave a crude oil which

Sources & evidence

ORD record
ord-92b027a91ca44f40a12b15aa5e3865a0
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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