Hydrochloric Acid → HCID 67212441, compound

HRID 1695709Notes

Reaction equation

HRID 1695709 reaction equation
C1(S([N:10]2[CH2:17][CH:16]3[N:18]([CH3:19])[CH:12]([CH2:13][O:14][CH2:15]3)[CH2:11]2)(=O)=O)C=CC=CC=1.C1(C)C=CC=CC=1.[ClH:27]>C1(C)C(C)=CC=CC=1>[ClH:27].[CH3:19][N:18]1[CH:12]2[CH2:11][NH:10][CH2:17][CH:16]1[CH2:15][O:14][CH2:13]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 67212526HCID 67212526, compound

Product 1

HCID 67212441HCID 67212441, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of the above described 7-benzenesulfonyl-9-methyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane (880 mg, 3.177 mmol) in xylene (20 ml) was added sodium dihydro-bis(2-methoxyethoxy)aluminate in toluene (2.423 ml, 7.947 mmol) and the mixture was stirred at 140° C. for 18 h. Cooled to 23° C., poured into 2 M HCl, extracted twice with tert-butyl methyl ether, the aqueous layer was made alkaline with 10 M NaOH-sol., extracted twice with tert-butyl methyl ether, the combined organic layer was dried over sodium sulfate, filtered, to the filtrate was added ethanol (5 ml) and chlorotrimethylsilane (ca. 0.5 ml) and all volatiles were removed in vacuum to give the title compound as a colorless oil (190 mg, 43%), MS (ISP) m/e=143.2 [(M+H)+].

Workup

  1. additionTo a mixture of the
  2. temperatureCooled to 23° C.
  3. extractionextracted twice with tert-butyl methyl ether
  4. extraction, extracted twice with tert-butyl methyl ether
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered, to the filtrate
  7. additionwas added ethanol (5 ml) and chlorotrimethylsilane (ca. 0.5 ml)
  8. customall volatiles were removed in vacuum

Sources & evidence

ORD record
ord-618f761bf5474e9883633989c9799d96
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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