Hydrochloric Acid → N-(4-Oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfonamide hydrochloride

HRID 1093901Notes

Reaction equation

HRID 1093901 reaction equation
C([N:9]1[CH2:14][CH2:13][C:12]2([CH2:23][C:22](=[O:24])[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:20]=3)[O:15]2)[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.C(O)C.[ClH:33].CO>ClCCl>[ClH:33].[O:24]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:20]=2)[O:15][C:12]2([CH2:11][CH2:10][NH:9][CH2:14][CH2:13]2)[CH2:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 887MethanolHCID 15026085N-(1'-benzoyl-4-oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfonamide2×

Product 1

HCID 19045253N-(4-Oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfonamide hydrochlorideYield 114%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
87.5 °C

Procedure

N-(1′-Benzoyl-4-oxospiro[chroman-2,4′-piperidine]-6-yl)methanesulfonamide (10, 0.81 g, 1.95 mmol) was suspended in a mixture of absolute ethanol (10 mL) and 6 M aqueous hydrochloric acid (10 mL) and stirred at 85-90° C. in an oil bath. After 1 hour the oil bath temperature was increased to 95° C. After ˜3.5 hours at 95° C. the reaction was allowed to cool to room temperature. TLC (silica gel, 10% methanol in dichloromethane, UV visualization) showed no remaining starting material [Rf (10)=0.65−0.7]. Solvent was removed under reduced pressure on a rotary evaporator. Ethanol was added to the residue and then evaporated to dryness under reduced pressure on a rotary evaporator. The ethanol addition and evaporation to dryness was repeated two more times. The residue was dried in vacuo to afford 0.77 g (114% yield) of N-(4-oxospiro[chroman-2,4′-piperidine]-6-yl)methanesulfonamide hydrochloride (11) as a light yellow solid that was homogeneous by TLC [silica gel, 10% methanol in dichloromethane containing a small amount of concentrated aqueous ammonium hydroxide, UV visualization, Rf (11)=0.12−0.19]. Mass spec: m/z=311.2 [M+H]+

Workup

  1. temperatureAfter 1 hour the oil bath temperature was increased to 95° C
  2. temperatureto cool to room temperature
  3. customSolvent was removed under reduced pressure on a rotary evaporator
  4. additionEthanol was added to the residue
  5. customevaporated to dryness under reduced pressure on a rotary evaporator
  6. additionThe ethanol addition and evaporation to dryness
  7. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-72dc89e4c6264670ab8d88f01c307fd2
Source dataset
uspto-grants-2012_03
Patent number
US08133695B2

Reaction notes

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