Sodium Chloride → Methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate

HRID 418001Notes

Reaction equation

HRID 418001 reaction equation
[C:1]([N:8]1C=CN=C1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[S:2].[OH2:13].[NH2:14]N.[Cl-].[Na+].[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>>[NH:8]([C:1]([N:3]1[CH2:4][CH2:21][CH:20]([C:19]([O:18][CH3:22])=[O:13])[CH2:6][CH2:7]1)=[S:2])[NH2:14]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 24855846Methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylateYield 114%

Procedure

Methyl isonipecotinate (1.0 g, 6.98 mmol) in tetrahydrofuran was mixed with thiocarbonyldiimidazole (1.24 g, 6.98 mmol) at room temperature and then stirred at room temperature for 1.5 hours and stirred with hydrazine monohydrate (700 mg, 14.0 mmol) for another 4 hours. The reaction solution was mixed with saturated aqueous sodium chloride and extracted with ethyl acetate and chloroform. The extract was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated to give the crude preparation of the desired product (114% yield).

Workup

  1. extractionextracted with ethyl acetate and chloroform
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customto give the crude

Sources & evidence

ORD record
ord-20fb03cc9ac84a8eb2c1353394d0adfe
Source dataset
uspto-grants-2012_01
Patent number
US08093251B2

Reaction notes

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