3-Pyridinemethanamine → HCID 2826565, compound

HRID 620510Notes

Reaction equation

HRID 620510 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.FC1C=CC(CN2C3C=CC=CC=3N=C2NC2CCN(CC[N:35]=[C:36]=[S:37])CC2)=CC=1>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:36](=[S:37])[NH2:35])[CH:2]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 128917531-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]1H-benzimidazol-2-amine

Product 1

HCID 2826565HCID 2826565, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 part of 3-pyridinemethanamine, 3.9 parts of 1-(4-fluorophenylmethyl)-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-1H-benzimidazol-2-amine and 45 parts of tetrahydrofuran was stirred for 4 hours at room temperature. The reaction mixture was evaporated in vacuo. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (94:6 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane, yielding 3.4 parts (65.7%) of N-[2-[4-[[1-(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]-ethyl]-N'-(3-pyridinylmethyl)thiourea; mp. 147.2° C. (compound 102).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customThe residue was purified by column-chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol (94:6 by volume) as eluent
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-3cab0d3d004d40e4b6444ebafdbb5ca1
Source dataset
uspto-grants-1989_04
Patent number
US04820822

Reaction notes

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