Ammonia → HCID 20379513, compound

HRID 2051692Notes

Reaction equation

HRID 2051692 reaction equation
[Cl:1][C:2]1[C:34]([Cl:35])=[CH:33][C:5]2[N:6]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][CH:18]([OH:32])[CH2:19][O:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30]C)=O)=[CH:23][CH:22]=4)[CH2:12]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[NH3:36]>CO>[Cl:1][C:2]1[C:34]([Cl:35])=[CH:33][C:5]2[N:6]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][CH:18]([OH:32])[CH2:19][O:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH2:36])=[O:30])=[CH:23][CH:22]=4)[CH2:12]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20379495HCID 20379495, compound

Product 1

HCID 20379513HCID 20379513, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 11 parts of methyl 4-{3-[3-(5,6-dichloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-ylmethyl)-1-piperidinyl]-2-hydroxypropoxy}benzeneacetate and 800 parts of methanol saturated with ammonia is stirred and heated in an autoclave at 110° C. and at a pressure of 85.7 lbs/sq. inch. The reaction mixture is cooled and evaporated. The residue is stirred in 4-methyl-2-pentanone. The product is filtered off and purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone and a small amount of 2-propanol. The product is filtered off and dried, yielding 2.7 parts (25%) of 4-{3-[3-(5,6-dichloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-ylmethyl)-1-piperidinyl]-2-hydroxypropoxy}benzeneacetamide; mp. 147.9° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated
  3. stirringThe residue is stirred in 4-methyl-2-pentanone
  4. filtrationThe product is filtered off
  5. custompurified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated
  9. customThe residue is crystallized from 4-methyl-2-pentanone
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-3923e9fa3bc34533a3c7e5103fcbf924
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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