Hydrochloric Acid → 7-benzenesulfonyl-4-piperidin-4-yl-3,4-dihydro-2H-benzo[1,4]oxazine hydrochloride

HRID 2224079Notes

Reaction equation

HRID 2224079 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][C:22]([S:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[CH:23][C:18]=3[O:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:33]>C(O)C>[ClH:33].[C:27]1([S:24]([C:22]2[CH:21]=[CH:20][C:19]3[N:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH2:15][CH2:16][O:17][C:18]=3[CH:23]=2)(=[O:26])=[O:25])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 684330714-(7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 684350507-benzenesulfonyl-4-piperidin-4-yl-3,4-dihydro-2H-benzo[1,4]oxazine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.111 g, 0.242 mmol) was dissolved in 5 mL ethyl alcohol and brought to reflux. To the solution was added ethanolic hydrogen chloride (2 mL of a 2N solution, 4.0 mmol) and reflux continued for 0.5 hours. The solution is concentrated to 1 mL and ethyl ether (10 mL) is added until a white precipitate is observed. Filtration gave 0.085 g (quantitative) of 7-benzenesulfonyl-4-piperidin-4-yl-3,4-dihydro-2H-benzo[1,4]oxazine hydrochloride as a white powder. MS: 359 (M+H)+, mp: 251.9-253.2° C.

Workup

  1. temperatureto reflux
  2. temperaturereflux
  3. concentrationThe solution is concentrated to 1 mL and ethyl ether (10 mL)
  4. additionis added until a white precipitate
  5. filtrationFiltration

Sources & evidence

ORD record
ord-8da2b532db4649ef8cb1d19f0bb46a6c
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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