Hydrochloric Acid → N-(1-(4-oxocyclohexyl)propyl)methanesulfonamide

HRID 2175605Notes

Reaction equation

HRID 2175605 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:12][CH3:13])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC#N>[O:4]=[C:5]1[CH2:6][CH2:7][CH:8]([CH:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:12][CH3:13])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58562472HCID 58562472, compound

Product 1

HCID 58562881N-(1-(4-oxocyclohexyl)propyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(1-1,4-dioxaspiro[4.5]decan-8-ylpropyl)methanesulfonamide (as prepared in the previous step, 38 mg, 0.14 mmol, 1.00 equiv) in CH3CN (5 mL) and HCl (2M, 1 mL) was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 10 mL of aq. sodium bicarbonate (1M). The resulting solution was extracted with 2×20 mL of dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum to give the title compound as a yellow oil.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additionThe residue was diluted with 10 mL of aq. sodium bicarbonate (1M)
  3. extractionThe resulting solution was extracted with 2×20 mL of dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d213c9948f5d4cd7b28144831f60bda6
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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