Ammonia → HCID 13769777, compound

HRID 477665Notes

Reaction equation

HRID 477665 reaction equation
[NH3:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[C:11]2[NH:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]=[C:29]=[S:30])[CH2:22][CH2:21]2)=[CH:5][CH:4]=1>CO>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[C:11]2[NH:19][CH:20]2[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][NH:28][C:29]([NH2:1])=[S:30])[CH2:24][CH2:25]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 128917531-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]1H-benzimidazol-2-amine

Product 1

HCID 13769777HCID 13769777, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 120 parts of methanol saturated with ammonia and 4.1 parts of 1-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine was stirred overnight at room temperature. The reaction mixture was evaporated and the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume), saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was suspended in 1,1'-oxybisethane. The product was filtered off and crystallized from acetonitrile, yielding 1.1 parts (26%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiourea; mp. 186.1° C. (intermediate 149).

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 (95:5 by volume)
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. filtrationThe product was filtered off
  7. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-74c3c3d4be7a4393abd527073d925269
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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