Piperazine → HCID 178523109, compound

HRID 1988385Notes

Reaction equation

HRID 1988385 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17](C=O)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].[OH-].[NH4+].C1(C)C=CC(S(CN=C=O)(=O)=O)=CC=1.[NH:38]1[CH2:43][CH2:42][NH:41][CH2:40]C1>C1COCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:43]2[N:38]=[CH:40][NH:41][CH:42]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5]

Participants

8

Reactant 4

HCID 4837PiperazineHCID 14923Ammonium HydroxideHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzeneHCID 865959112-chloro-5-formyl-N-(1-hydroxy-cycloheptylmethyl)-benzamide

Product 1

HCID 178523109HCID 178523109, compoundYield 21.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-5-formyl-N-(1-hydroxy-cycloheptylmethyl)-benzamide (50 mg, 0.16 mmol) and ammonium hydroxide (0.5 mL, 0.44 mmol) in THF (5 mL) was stirred at room temperature for 6 h. p-Toluenesufonylmethylisocyanate (21 mg, 0.11 mmol) and piperazine (14 mg, 0.16 mmol) were added and the mixture was stirred at room temperature for 5 d. The mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in HCl (20 mL, 1M) and washed with ethyl acetate. The aqueous layer was saponified to pH 12 with sodium hydroxide (6M) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a white solid (12 mg).

Workup

  1. additionwere added
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in HCl (20 mL, 1M)
  7. washwashed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ebcaaf2d0d1400cb43061bd0141dfe1
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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