Hydrochloric Acid → HCID 18913475, compound

HRID 962900Notes

Reaction equation

HRID 962900 reaction equation
OS(O)(=O)=O.O[CH2:7][CH:8]([NH:10][CH:11]([CH3:21])[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[OH:13])[CH3:9].[OH-].[Na+].[ClH:24]>ClCCl.C(OCC)C>[ClH:24].[F:20][C:16]1[CH:15]=[C:14]([CH:12]2[O:13][CH2:7][CH:8]([CH3:9])[NH:10][CH:11]2[CH3:21])[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 54111996HCID 54111996, compound

Product 1

HCID 18913475HCID 18913475, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To concentrated H2SO4 (75 ml) was added a solution of (1R*, 2S*)-2-[[(1RS)-2-hydroxy-1-methylethyl]amino]-1-(3-fluorophenyl)propanol (21.6 g, 0.095 mole) in dichloromethane (100 ml) at 0° C. The resulting mixture was stirred for 16 hours at room temperature and diluted with ice water. The aqueous phase was basified with 40% aqueous sodium hydroxide and extracted with diethyl ether. The diethyl ether layers were combined, washed with brine, dried (sodium sulfate), and concentrated under reduced pressure to yield the crude reaction product as the free base. The crude product was dissolved in diethyl ether and treated with ethereal hydrogen chloride. Recrystallization from ethanol-diethyl ether mixtures gave 17.7 g of (+-)-(2R*, 3R*, 5S*)-2-(3-fluorophenyl)-3,5-dimethylmorpholine hydrochloride as a white solid, m.p. 268°-269° C.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customto yield the crude
  6. customreaction product as the free base
  7. customRecrystallization from ethanol-diethyl ether mixtures

Sources & evidence

ORD record
ord-273cd3b851024d82afde225f52a987fc
Source dataset
uspto-grants-1998_06
Patent number
US05760224

Reaction notes

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