Triethylamine → HCID 19079064, compound

HRID 1735865Notes

Reaction equation

HRID 1735865 reaction equation
[CH2:1]([O:3][C:4]1(CCNC)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH3:2].[CH2:23]([N:25]([CH2:28]C)CC)[CH3:24].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH2:1]([O:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([CH2:24][CH2:23][N:25]([CH3:28])[S:31]([CH3:30])(=[O:33])=[O:32])[C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19079051HCID 19079051, compound

Product 1

HCID 19079064HCID 19079064, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The following compound was obtained according to a similar manner: ##STR52## MS (FAB) m/e 296 (M+1 for free base) ##STR53## For Compound IN: Dissolved N-[2-(5-ethoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)ethyl]-N-methylamine (150 mg, 0.508 mmol)in 5 mL of dry dichloromethane. Cooled to 0° C. under a nitrogen atmosphere, and added triethylamine (0.14 mL, 0.10 g, 1.0 mmol) and then methanesulfonyl chloride (0.06 mL, 0.089 g, 0.76 mmol) dropwise via syringe. Stirred at 0° C. for 90 mins. Added water, and extracted with dichloromethane. Washed the combined organic extracts with sodium phosphate monobasic, 1N NaOH, and then saturated NaCl. Dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography eluting with 9:1 hexane:ethyl acetate. Combined appropriate fractions, and evaporated to solid. Recrystallized from ethyl acetate-hexane to give 92 mg (48% yield) of N-[2-(5-ethoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptenyl)ethyl]-N-methylmethanesulfonamide as a white solid.

Workup

  1. customThe following compound was obtained
  2. extractionAdded water, and extracted with dichloromethane
  3. washWashed the combined organic extracts with sodium phosphate monobasic, 1N NaOH
  4. dry with materialDried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurified crude product by flash chromatography
  8. washeluting with 9:1 hexane
  9. customevaporated to solid
  10. customRecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3fbab44286eb4152b036a2a608b20944
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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