Carbon Disulfide → 4-isothiocyanato-1-methylpiperidine

Reaction equation

O1CCCC1.[CH3:6][N:7]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]1.[C:14](=S)=[S:15]>>[N:13]([CH:10]1[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]1)=[C:14]=[S:15]

Participants

Reactant 3

HCID 6348Carbon Disulfide

HCID 8028Tetrahydrofuran

HCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 157187604-isothiocyanato-1-methylpiperidineYield 100%

Conditions

Temperature: -10 °C

Procedure

To a stirred mixture of 412 parts of N,N'-methanetetraylbis[cyclohexanamine] and 2225 parts of tetrahydrofuran there were added dropwise 1092 parts of carbon disulfide and, after cooling to -10° C., portionwise 228 parts of 1-methyl-4-piperidinamine. The whole was stirred for 1 hour at room temperature and was then evaporated. The residue was recrystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 416.6 parts (100%) of 4-isothiocyanato-1-methylpiperidine (interm. 16).