Carbon Disulfide → 1-(2-furanylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine
Reaction equation
[C:1](=[S:3])=S.[NH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:18]([CH2:19][C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[C:17]3[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=3[N:15]=2)[CH2:9][CH2:8]1>O1CCCC1>[O:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[CH2:19][N:18]1[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[N:15]=[C:14]1[NH:13][CH:10]1[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][N:4]=[C:1]=[S:3])[CH2:8][CH2:9]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred and cooled (-10° C.) mixture of 12.6 parts of carbon disulfide, 5.2 parts of N,N'-methanetetraylbis[cyclohexanamine]and 45 parts of tetrahydrofuran was added dropwise a solution of 8.5 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(2-furanylmethyl)-1H-benzimidazol-2-amine in 45 parts of tetrahydrofuran. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was evaporated and the residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 6.7 parts of 1-(2-furanylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine (intermediate 123).
Workup
- temperaturecooled
- stirringUpon completion, stirring
- customThe reaction mixture was evaporated
- customthe residue was purified by column chromatography over silica gel
- customThe pure fractions were collected
- customthe eluent was evaporated
- customThe residue was crystallized from acetonitrile
Sources & evidence
- ORD record
- ord-603a517fce5b40f8a4820140e2b9cf26
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04695569
Reaction notes
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