Methyl isothiocyanate → HCID 86663381, compound

HRID 1193392Notes

Reaction equation

HRID 1193392 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[CH3:5][N:6]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl>[CH3:5][N:6]([CH:17]1[CH2:18][CH2:19][N:20]([C:3](=[S:4])[NH:2][CH3:1])[CH2:21][CH2:22]1)[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 18677746Benzyl methyl(piperidin-4-yl)carbamate

Product 1

HCID 86663381HCID 86663381, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl isothiocyanate (500 mg, 6.8493 mmol, 1 eq) in dichloromethane (4 ml) was added dropwise over a period of 5 min to a solution of benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (1.7 g, 6.8493 mmol, 1 eq). When the addition was complete, the reaction mixture was stirred for 20 hours at room temperature. Concentration under reduced pressure was then carried out and the crude product was purified by column chromatography (silica gel, 2% methanol in dichloromethane). Yield: 45% (1 g, 3.115 mmol)

Workup

  1. additionWhen the addition
  2. concentrationConcentration under reduced pressure
  3. customthe crude product was purified by column chromatography (silica gel, 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6ac9c05858274756aebffa91cb4db4c4
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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