Tetrahydrofuran → HCID 54416378, compound

HRID 1900248Notes

Reaction equation

HRID 1900248 reaction equation
CNCC([CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][O:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)CCC.C([N:25]([CH2:28][CH3:29])[CH2:26]C)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].[CH2:36]1[CH2:40]OC[CH2:37]1>>[C:22]1([CH:29]([CH2:37][CH2:36][CH3:40])[CH2:28][N:25]([CH3:26])[C:31](=[O:32])[O:33][CH2:34][CH3:35])[C:9]2[CH2:8][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][O:11][C:10]=2[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 15388862HCID 15388862, compound

Product 1

HCID 54416378HCID 54416378, compoundYield 73%

Procedure

Dissolved N-methyl-2-[6,11-dihydro-dibenzo[b,e]oxepin-11-yl]-pentanamine (0.50 g, 1.70 mmol)in 20 mL of dry THF. Added triethylamine (0.28 mL, 0.21 g, 2.02 mmol) and ethyl chloroformate (0.18 mL, 0.20 g, 1.86 mmol). Stirred at room temperature for 16 hours. Added water, and extracted with ether. 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 0.45 g (73% yield) of ethyl [2-(6,11 -dihydro-dibenzo[b,e]oxepin-1-yl)-pentyl]-methylcarbamate as a colorless oil.

Workup

  1. extractionAdded water, and extracted with ether
  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-ff5a55f65fa642989a5dc5f96888099d
Source dataset
uspto-grants-1996_11
Patent number
US05574173

Reaction notes

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