Hydrochloric Acid → HCID 57288011, compound

HRID 1418371Notes

Reaction equation

HRID 1418371 reaction equation
[CH2:1]1[O:21][C:4](O)([C:5]2[CH:10]=[CH:9][C:8]([C:11]([N:13]3[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)=[O:12])=[CH:7][CH:6]=2)[O:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[OH:41].Cl>CN(C=O)C>[CH2:1]1[O:21][C:4]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[OH:41])([C:5]2[CH:6]=[CH:7][C:8]([C:11]([N:13]3[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)=[O:12])=[CH:9][CH:10]=2)[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 58012-AminophenolHCID 682631,1'-CarbonyldiimidazoleHCID 86753880HCID 86753880, compound

Product 1

HCID 57288011HCID 57288011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-oxopiperidinocarbonyl)benzoic acid ethylene ketal (291 mg, 1 mmol) in DMF (3 ml) was treated with 1,1'-carbonyldiimidazole (162 mg, 1 mmol) and stirred for 30 min. 2-Aminophenol (109 mg, 1 mmol) was added and stirring continued for 22 h. The mixture was acidified with dilute HCl, extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash column chromatography on silica, eluting with ethyl acetate, to furnish a clear glass, MS (+CI) 383 ([M+H]+).

Workup

  1. stirringstirring
  2. waitcontinued for 22 h
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with ethyl acetate
  9. customto furnish a clear glass, MS (+CI) 383 ([M+H]+)

Sources & evidence

ORD record
ord-6f0069fced9d4d87b8f55061dc491ed4
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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