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Methyl isothiocyanate → 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-N-methyl-[1,3'-bipiperidine]-1'-carbothioamide

HRID 280347
Notes
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Reaction equation

HRID 280347 reaction equation
[N:1]([CH3:4])=[C:2]=[S:3].[N:5]1([CH:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[N:13]=2)[CH2:7][CH2:6]1>O1CCCC1>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:16]2[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[N:13]=[C:12]2[NH:11][CH:8]2[CH2:7][CH2:6][N:5]([CH:29]3[CH2:34][CH2:33][CH2:32][N:31]([C:2](=[S:3])[NH:1][CH3:4])[CH2:30]3)[CH2:10][CH2:9]2)=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 15614721N-([1,3'-bipiperidin]-4-yl)-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine

Product 1

HCID 136538844-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-N-methyl-[1,3'-bipiperidine]-1'-carbothioamideYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.8 parts of isothiocyanatomethane, 4 parts of N-([1,3'-bipiperidin]-4-yl)-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine and 90 parts of tetrahydrofuran was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 3.7 parts (77%) of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-N-methyl-[1,3'-bipiperidine]-1'-carbothioamide; mp. 218.8° C. (compound 37).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-25d1a3078bd74e72a9a2f6ba967541f0
Source dataset
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04588722

Reaction notes

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