Hydrochloric Acid → HCID 86674090, compound

HRID 337236Notes

Reaction equation

HRID 337236 reaction equation
C([O:5][C:6](=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][NH:24][C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.Cl.[CH:36](N(C(C)C)CC)(C)[CH3:37].C(Cl)(=O)C=C>O1CCOCC1.C(Cl)Cl>[C:27]1([CH2:26][C:25]([NH:24][CH2:23][C:20]2[CH:19]=[CH:18][C:17]([S:14]([N:11]3[CH2:10][CH2:9][CH:8]([NH:7][C:6](=[O:5])[CH:36]=[CH2:37])[CH2:13][CH2:12]3)(=[O:15])=[O:16])=[CH:22][CH:21]=2)=[O:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 71060168HCID 71060168, compound

Product 1

HCID 86674090HCID 86674090, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

{1-[4-(Phenylacetylamino-methyl)-benzenesulfonyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (0.15 g, 0.31 mmol) was suspended in a 4M solution of HCl in Dioxane (10 ml). The resulting suspension was stirred at room temperature for 3 hours. After this time the solution was concentrated under vacuum and the resulting residue dissolved in THF (10 ml). To this solution was added diisopropylethylamine (0.25 ml, 1.54 mmol) was added in one portion, followed by the drop wise addition of acryloyl chloride (0.03 ml, 0.38 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (20 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered, concentrated and the resulting residue was purified by flash column chromatography (elution: 100% DCM to 95% DCM, 5% Methanol) to give the title compound (0.025 g, 18% yield) as a white solid.

Workup

  1. concentrationAfter this time the solution was concentrated under vacuum
  2. dissolutionthe resulting residue dissolved in THF (10 ml)
  3. additionwas added in one portion
  4. stirringthe mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours
  5. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe resulting residue was purified by flash column chromatography (elution: 100% DCM to 95% DCM, 5% Methanol)

Sources & evidence

ORD record
ord-bd39b8ed96c4478ea3fb277d1faacfc2
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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