Triethylamine → HCID 45118489, compound

HRID 2402340Notes

Reaction equation

HRID 2402340 reaction equation
Cl.[F:2][C:3]1([F:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.C1N=C[N:19]([C:22](N2C=NC=C2)=[S:23])C=1>C1COCC1>[F:2][C:3]1([F:9])[CH2:8][CH2:7][N:6]([C:22]([NH2:19])=[S:23])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 27583514,4-Difluoropiperidine hydrochloride

Product 1

HCID 45118489HCID 45118489, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Commercially available 4,4-difluoropiperidine hydrochloride (883 mg, 5.60 mmol) and triethylamine (0.85 mL, 6.10 mmol) were added to a solution of 1,1-thiocarbonyldiimidazole (1.05 g, 5.89 mmol) in THF (20 mL) under ice-cooling, followed by stirring at room temperature for 3 hr in an argon atmosphere. The reaction solution was concentrated. Concentrated aqueous ammonia (30 mL) was added to the residue, followed by stirring overnight at room temperature. The precipitated crystals were collected by filtration, washed with water, and dried to obtain 4,4-difluoropiperidinothiocarboxamide (850 mg, 4.72 mmol) as a light yellow powder.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. additionConcentrated aqueous ammonia (30 mL) was added to the residue
  4. stirringby stirring overnight at room temperature
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-52d07266d4424bec879d2720bbc81298
Source dataset
uspto-grants-2014_08
Patent number
US08796320B2

Reaction notes

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