1,1'-Thiocarbonyldiimidazole → HCID 57181357, compound

HRID 2172833Notes

Reaction equation

HRID 2172833 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](N1C=CN=C1)(N1C=CN=C1)=[S:17]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]=[C:16]=[S:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 57181357HCID 57181357, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(t-butyloxycarbonyl)-4-(aminomethyl)piperidine (2.14 g) in N,N-dimethylformamide (20 ml) was added 1,1′-thiocarbonyldiimidazole (1.87 g), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was poured into ice water (100 ml), and extracted with ethyl acetate (100 ml). The extract was washed successively with 0.5M hydrochloric acid, 1M aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to give [1-(t-butyloxycarbonyl)piperidin-4-yl]methyl isothiocyanate (1.64 g).

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe extract was washed successively with 0.5M hydrochloric acid, 1M aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-774747abefa14d439070536ab6b79865
Source dataset
uspto-grants-2015_06
Patent number
US09056862B2

Reaction notes

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