Carbon Disulfide → 1-Acetyl-4-(isothiocyanatomethyl)piperidine

HRID 1761478Notes

Reaction equation

HRID 1761478 reaction equation
[C:1](=[S:3])=S.[C:4]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9][CH2:8]1)(=[O:6])[CH3:5]>O1CCCC1>[C:4]([N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][N:14]=[C:1]=[S:3])[CH2:11][CH2:12]1)(=[O:6])[CH3:5]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 126870221-(4-(Aminomethyl)piperidin-1-yl)ethan-1-one

Product 1

HCID 156115901-Acetyl-4-(isothiocyanatomethyl)piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (-10° C.) mixture of 41.6 parts of N,N'-methanetetraylbis[cyclohexanamine], 101 parts of carbon disulfide and 450 parts of tetrahydrofuran was added dropwise a solution of 31.2 parts of 1-acetyl-4-piperidinmethanamine in 90 parts of tetrahydrofuran. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was evaporated, 2,2'-Oxybispropane was added to the residue. The precipitate was filtered off and the filtrate was evaporated, yielding 40 parts (100%) of 1-acetyl-4-(isothiocyanatomethyl) piperidine as a residue (intermediate 10).

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. customThe reaction mixture was evaporated
  4. addition2,2'-Oxybispropane was added to the residue
  5. filtrationThe precipitate was filtered off
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-226bfe3968e14ecdbaeda411b2888494
Source dataset
uspto-grants-1989_05
Patent number
US04826848

Reaction notes

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