Water → HCID 131719469, compound

HRID 1735853Notes

Reaction equation

HRID 1735853 reaction equation
CNC[CH2:4][C:5]1([CH2:20][CH:21]=[CH2:22])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[CH2:23]([N:25](CC)CC)C.Cl[C:31]([O:33][CH2:34]C)=[O:32].O>C1COCC1>[CH2:20]([C:5]1([CH2:4][CH2:34][O:33][C:31](=[O:32])[NH:25][CH3:23])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)[CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19079045HCID 19079045, compound

Product 1

HCID 131719469HCID 131719469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolved 10,11-dihydro-N-methyl-5-(2-propenyl)-5H-dibenzo[a,d]cycloheptene-5-ethanamine (0.50 g, 1.72 mmol) in 20 mL of dry THF. Added triethylamine (0.29 mL, 0.21 g, 2.06 mmol) and ethyl chloroformate (0.18 mL, 0.20 g, 1.88 mmol). Stirred at room temperature for 5 hours. Added 50 mL of water, and extracted with dichloromethane. Dried combined organic extracts with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with dichloromethane. Combined appropriate fractions, and evaporated to give 0.50 g (81% yield) of ethyl N-[2-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]ethyl-N-methylcarbamate.

Workup

  1. extractionextracted with dichloromethane
  2. customDried
  3. filtrationfiltered
  4. customevaporated
  5. customPurified crude product by flash chromatography on silica gel eluting with dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-c721f8b29ae043f18c15e140a8ae9ed4
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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