Triethylamine → HCID 19079064, compound

HRID 963976Notes

Reaction equation

HRID 963976 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

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-methyl-methanesulfonamide as a white, solid.

Workup

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

Sources & evidence

ORD record
ord-de2bb33f5f1741d38f252de2e8c19020
Source dataset
uspto-grants-1998_06
Patent number
US05767120

Reaction notes

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