Hydrochloric Acid → HCID 67277667, compound

HRID 1695705Notes

Reaction equation

HRID 1695705 reaction equation
C1(S([N:10]2[CH2:15][CH:14]([CH2:16][O:17][CH3:18])[N:13]([CH3:19])[CH:12]([CH2:20][O:21][CH3:22])[CH2:11]2)(=O)=O)C=CC=CC=1.C1(C)C=CC=CC=1.[ClH:30]>C1(C)C(C)=CC=CC=1>[ClH:30].[CH3:22][O:21][CH2:20][CH:12]1[CH2:11][NH:10][CH2:15][CH:14]([CH2:16][O:17][CH3:18])[N:13]1[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 67277826HCID 67277826, compound

Product 1

HCID 67277667HCID 67277667, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of the above described (2SR,6SR)-4-benzenesulfonyl-2,6-bis-methoxymethyl-1-methyl-piperazine (910 mg, 2.771 mmol) in xylene (20 ml) was added sodium dihydro-bis(2-methoxyethoxy)aluminate in toluene (2.154 ml, 7.065 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 (350 mg, 56%), MS (ISP) m/e=189.3 [(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-287a6cae7df44b6eb19b5be9fd208ec0
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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