p-Toluenesulfonic acid → HCID 19911539, compound

HRID 1533956Notes

Reaction equation

HRID 1533956 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH:13][C:14](=O)[CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.CC1C=CC=CC=1C>O>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[N:13]=[C:14]1[CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 54008357HCID 54008357, compound

Product 1

HCID 19911539HCID 19911539, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 37.8 parts of N-[3-[(2-ethoxyethyl)amino]-4-pyridinyl]-4-(phenylmethyl)-1-piperazineacetamide, 0.1 parts of 4-methylbenzenesulfonic acid and 450 parts of dimethylbenzene was stirred for 16 hours at reflux temperature using a water separator. The reaction mixture was evaporated and the residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (93:7 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 20.2 parts (56.1%) of 3-(2-ethoxyethyl)-2-[[4-(phenylmethyl)-1-piperazinyl]methyl]-3H-imidazo[4,5-c]pyridine as a residue (compound 11).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography over silica gel using
  4. additiona mixture of dichloromethane and methanol (93:7 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-840db9ade60c42debe5804f26e2ff922
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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