Sodium Carbonate → HCID 23453173, compound

HRID 1277642Notes

Reaction equation

HRID 1277642 reaction equation
[ClH:1].[CH3:2][O:3][C:4]([CH2:6][CH2:7][CH:8]1[CH:17]2[N:12]([CH2:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:16]=32)[CH2:11][CH2:10][CH2:9]1)=[O:5].[C:25](=O)([O-])[O-].[Na+].[Na+]>ClCCl>[ClH:1].[CH2:2]([O:3][C:4]([CH2:6][CH2:7][CH:8]1[CH:17]2[N:12]([CH2:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:16]=32)[CH2:11][CH2:10][CH2:9]1)=[O:5])[CH3:25]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 23453180HCID 23453180, compound

Product 1

HCID 23453173HCID 23453173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.35 g (1 mmole) of 1-(2'-methoxycarbonyl-ethyl)-1,2,3,4,6,7.12,12b-octahydro-indolo[2,3-a]quinolizine hydrochloride are partitioned between 10 ml of dichloromethane and 3 ml of 5% aqueous sodium carbonate solution, and the aqueous phase is extracted with 2×3 ml of dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered, and the filtrate is evaporated. The oily residue is dissolved in 15 ml of absolute ethanol, 50 mg of sodium ethoxide are added to the solution, and the mixture is boiled for 2 hours. Thereafter the mixture is cooled, the sodium ethoxide is decomposed with glacial acetic acid, and the solution is evaporated to dryness in vacuo. The residue is admixed with 10 ml of 5% aqueous sodium carbonate solution, and the mixture is extracted with 20 ml of dichloromethane. The organic phase is filtered, the filtrate is dried over magnesium sulfate, filtered again, and then evaporated in vacuo to dryness. The obtained 0.30 g of oily residue are dissolved in 2 ml of ethanol, the solution is acidified to pH 6 with ethanolic hydrochloric acid, the separated salt is filtered off, washed with ethanol and ether, and dried.

Workup

  1. extractionthe aqueous phase is extracted with 2×3 ml of dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. dissolutionThe oily residue is dissolved in 15 ml of absolute ethanol
  6. addition50 mg of sodium ethoxide are added to the solution
  7. temperatureThereafter the mixture is cooled
  8. customthe solution is evaporated to dryness in vacuo
  9. extractionthe mixture is extracted with 20 ml of dichloromethane
  10. filtrationThe organic phase is filtered
  11. dry with materialthe filtrate is dried over magnesium sulfate
  12. filtrationfiltered again
  13. customevaporated in vacuo to dryness
  14. dissolutionThe obtained 0.30 g of oily residue are dissolved in 2 ml of ethanol
  15. filtrationthe separated salt is filtered off
  16. washwashed with ethanol and ether
  17. customdried

Sources & evidence

ORD record
ord-95186e783c7f4a60aab38c6c9485f1e8
Source dataset
uspto-grants-1981_07
Patent number
US04278682

Reaction notes

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