Hydrochloric Acid → HCID 58641553, compound

HRID 2224073Notes

Reaction equation

HRID 2224073 reaction equation
C1(S([C:10]2[CH:25]=[CH:24][C:13]3[N:14]([C:18](=O)[CH2:19][CH2:20][NH:21][CH3:22])[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=O)=O)C=CC=CC=1.B.Cl.Cl.[C:29]1([S:35](C2C=CC3N(CCCNC)CCOC=3C=2)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(OCC)C.C1COCC1>[C:29]1([S:35]([C:25]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][CH2:20][NH:21][CH3:22])[C:13]=3[CH:24]=2)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 58641519HCID 58641519, compoundHCID 68432998HCID 68432998, compound

Product 1

HCID 58641553HCID 58641553, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 1 mL of freshly distilled THF was added 1-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-3-methylamino-propan-1-one (0.075 g, 0.210 mmol) and the resulting solution was cooled to 0° C. Borane:THF complex (0.315 mL of a 1 M solution, 0.315 mmol) was added dropwise over 2 minutes, during which offgassing was observed. The solution was warmed to reflux for 6 hours with stirring and then cooled to room temperature. Ethanolic hydrogen chloride (0.750 mL of a 2N solution, 1.5 mmol) was added dropwise accompanied by vigorous offgassing. The reaction mixture was refluxed for 2 hours at which time a white solid was observed in the solution. To the reaction mixture was added 2 mL diethyl ether and the solid was filtered and dried overnight under reduced pressure to give 0.045 g. of [3-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propyl]-methyl-amine hydrochloride as a fluffy white solid. MS: 347 (M+H)+, mp: 188.3-193.2° C. (as hydrochloride salt).

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 6 hours
  3. temperaturecooled to room temperature
  4. temperatureThe reaction mixture was refluxed for 2 hours at which time a white solid
  5. filtrationthe solid was filtered
  6. customdried overnight under reduced pressure
  7. customto give 0.045 g

Sources & evidence

ORD record
ord-f1562875d970450aaab020fd44dd19bf
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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