Acetic Acid → HCID 178502062, compound

HRID 437658Notes

Reaction equation

HRID 437658 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[C:16]([NH2:21])=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N=CO[CH2:25][NH:26][C:27](=[O:30])[O:28][CH3:29].C(O)(=O)C>ClC(Cl)Cl>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[NH:21][C:25]3=[N:26][C:27](=[O:30])[O:28][CH3:29])[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 93779N1-(1-benzylpiperidin-4-yl)benzene-1,2-diamineHCID 15037334Methyl (iminomethoxymethyl)-carbamate

Product 1

HCID 178502062HCID 178502062, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5 parts of N-[1-(phenylmethyl)-4-piperidinyl]-1,2-benzenediamine, 2.35 parts of methyl (iminomethoxymethyl)carbamate, 5 parts of acetic acid and 75 parts of trichloromethane is stirred and refluxed for 48 hours. The reaction mixture is evaporated and the residue is taken up in water. The solution is neutralized with ammonium hydroxide solution. The precipitated product is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 1.75 parts of methyl {1,3-dihydro-1-[1-(phenylmethyl)-4-piperidinyl]-2H-benzimidazol-2-ylidene}carbamate; mp. 169.7° C.

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe reaction mixture is evaporated
  3. customThe precipitated product is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated

Sources & evidence

ORD record
ord-85b2724c332741d8b0abd71422084ed1
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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