Water → HCID 53908090, compound

HRID 1731820Notes

Reaction equation

HRID 1731820 reaction equation
[CH3:1][N:2](C)[CH2:3][CH2:4][CH2:5][CH:6]1[C:10]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2.C(=O)(O)[O-].[Na+].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29].O>C1(C)C=CC=CC=1>[CH2:31]([O:30][C:28](=[O:29])[N:2]([CH2:3][CH2:4][CH2:5][CH:6]1[C:10]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[O:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)[CH3:1])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformate2×HCID 516892Sodium BicarbonateHCID 13732933HCID 13732933, compound

Product 1

HCID 53908090HCID 53908090, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture, kept under nitrogen, of 7.85 g of 3-(3-dimethylaminopropyl)-spiro[benzofuran-2(3H),1'-cycloheptane] and 11.7 g of powdered sodium bicarbonate in 250 ml of toluene was added 5.2 ml of ethyl chloroformate. The mixture was refluxed overnight and thereafter an additional 2.6 ml of ethyl chloroformate was added. The mixture was refluxed for another 5 hours and thereafter stirred overnight at room temperature. Water (250 ml) was then added with stirring. The organic phase was separated and washed successively with 2N-hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. This material was used as such for subsequent synthesis. The IR, NMR and Mass Spectra were in accord with the designated structure.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe mixture was refluxed for another 5 hours
  3. stirringwith stirring
  4. customThe organic phase was separated
  5. washwashed successively with 2N-hydrochloric acid, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo to an oil
  8. customsuch for subsequent synthesis

Sources & evidence

ORD record
ord-57427df7cdea4b2aae2e9d369c6421b3
Source dataset
uspto-grants-1986_11
Patent number
US04623657

Reaction notes

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