Sodium Chloride → Methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylate

HRID 1039120Notes

Reaction equation

HRID 1039120 reaction equation
[NH:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=O)[CH2:3][CH2:2]1.[C:11](C1NC=CN=1)(C1NC=CN=1)=[S:12].[OH2:23].[NH2:24][NH2:25].[Cl-].[Na+]>O1CCCC1>[NH:24]([C:11]([N:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:23])[CH2:3][CH2:2]1)=[S:12])[NH2:25]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 424914Methyl isonipecotateHCID 11412697Thiocarbonyl diimidazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl isonipecotate (1.0 g, 7.0 mmol) in tetrahydrofuran was added thiocarbonyl diimidazole (1.24 g, 6.98 mmol) at room temperature, and the reaction solution was stirred at room temperature for 1.5 hours and then stirred with hydrazine monohydrate (700 mg, 14.0 mmol) for 4 hours. After addition of saturated aqueous sodium chloride, the reaction solution was extracted with ethyl acetate and chloroform, and the extract was dried over anhydrous magnesium sulfate and concentrated to give the desired product (yield 114%).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate and chloroform
  2. dry with materialthe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6ba4db68f7dc4bf586d656f653f6d88a
Source dataset
uspto-grants-2013_10
Patent number
US08552031B2

Reaction notes

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