Carbon Disulfide → HCID 86744999, compound

HRID 256641Notes

Reaction equation

HRID 256641 reaction equation
[C:1](=[S:3])=S.[NH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][CH:6]1[CH3:15]>O1CCCC1>[N:4]([C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][C@H:6]1[CH3:15])=[C:1]=[S:3]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 19785295Methyl 4-amino-3-methylpiperidine-1-carboxylate

Product 1

HCID 86744999HCID 86744999, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (-10° C.) mixture of 138.6 parts of carbon disulfide, 113.8 parts of N,N'-methanetetraylbis[cyclohexanamine] and 450 parts of tetrahydrofuran were added dropwise 106 parts of methyl 4-amino-3-methyl-1-piperidinecarboxylate at this low temperature. The reaction mixture was allowed to attain room temperature. After stirring for 1 hour at room temperature, the mixture was evaporated and the residue was stirred in 2,2'-oxybispropane. The precipitate was filtered off and the filtrate was evaporated, yielding 141.1 parts (100%) of methyl cis-4-isothiocyanato-3-methyl-1-piperidinecarboxylate as a residue (interm. 28).

Workup

  1. temperaturecooled
  2. customto attain room temperature
  3. stirringAfter stirring for 1 hour at room temperature
  4. customthe mixture was evaporated
  5. stirringthe residue was stirred in 2,2'-oxybispropane
  6. filtrationThe precipitate was filtered off
  7. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2c27ff68673540239c9abcf74664f4fa
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

Loading…