Hydrochloric Acid → Dibenzo[b,e][1,4]oxazepine hydrochloride

HRID 365327Notes

Reaction equation

HRID 365327 reaction equation
CS(C)=O.C(Cl)(=O)C([Cl:8])=O.[CH:11]1[C:21]2[C:15](=[N:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[O:19][CH:20]=2)[CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+].Cl>ClCCl.CCOCC>[ClH:8].[CH:11]1[C:21]2[C:15](=[N:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[O:19][CH:20]=2)[CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 21955449Dibenzo[b,e][1,4]oxazepine

Product 1

HCID 131722018Dibenzo[b,e][1,4]oxazepine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

0.593 ml of DMSO (8.36 mmol) in 3 ml of dichloromethane was added to 0.365 ml (4.18 mmol) of oxalyl chloride in dichloromethane (15 ml) and the mixture was stirred at -78° C. for 15 min. 1.2 g (2.79 mmol) of (R)-(-)-5,11-dihydro-5-[1-[4-methoxyphenyl(2-hydroxy)ethyl]pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine in dichloromethane (5 ml) was added at -78° C. and after 2 hours 2.33ml (1.67 mmol) of triethylamine in 5 ml of dichloromethane was added. The mixture was warmed to room temperature and the mixture was poured in to saturated sodium hydrogen carbonate. The products were extracted with dichloromethane and the organic layer as washed with water, saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by silicagel column chromatography (n-hexane:ethyl acetate=5:1) to give pale yellow oil. By treating the oil with ether saturated with hydrogen chloride gave 452 mg (35%) of (R)-(-)-5,11-dihydro-5-[1-[4-methoxyphenyl (2-oxo)ethyl]pyrrolidin-2-yl]methyl]dibenzo[b,e][1,4]oxazepine hydrochloride as yellow powder.

Workup

  1. additionwas added
  2. temperatureThe mixture was warmed to room temperature
  3. extractionThe products were extracted with dichloromethane
  4. washthe organic layer as washed with water, saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silicagel column chromatography (n-hexane:ethyl acetate=5:1)
  8. customto give pale yellow oil

Sources & evidence

ORD record
ord-f7b44291be5345c390f71dd37296613e
Source dataset
uspto-grants-2000_10
Patent number
US06127361

Reaction notes

Loading…