Ammonia → HCID 20455130, compound

HRID 1263267Notes

Reaction equation

HRID 1263267 reaction equation
Cl([O-])(=O)(=O)=O.[CH2:6]([C:8]1([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:17]2[C:16]3[NH:18][C:19]4[C:24]([C:15]=3[CH2:14][CH2:13][N+:12]=2[CH2:11][CH2:10][CH2:9]1)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH3:7].N.[Br:32]Br>ClCCl>[CH3:27][O-:28].[CH2:6]([C:8]1([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:17]2[C:16]3[NH:18][C:19]4[C:24]([C:15]=3[CH2:14][CH2:13][N+:12]=2[CH2:11][CH2:10][CH2:9]1)=[CH:23][C:22]([Br:32])=[CH:21][CH:20]=4)[CH3:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 13241182HCID 13241182, compound

Product 1

HCID 20455130HCID 20455130, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.39 g. (10 mmoles) of 1-ethyl-1-(2'-methoxycarbonylethyl)-1,2,3,4,6,7-hexahydro-12H-indolo[2,3-a]quinolizin-5-ium perchlorate are shaken with a mixture of 5 ml. of 10% aqueous ammonia and 50 ml. of dichloromethane. The phases are separated, the organic phase is dried over 10 g. of solid anhydrous sodium sulfate, filtered, the filtrate is evaporated to a final volume of about 40 ml., and 0.1 g. of dry ferric chloride are added to this concentrate. 2.08 g. (0.67 ml., 13 mmoles) of elemental bromine are added dropwise, under vigorous stirring, to this mixture at 25° C. The addition takes place in 5 minutes. The reaction mixture is stirred at room temperature for 2 hours, thereafter it is rendered alkaline with 10 ml. of 10% aqueous ammonia, and the precipitated ferric hydroxide is filtered off. The organic phase of the filtrate is separated, dried over 10 g. of solid anhydrous sodium sulfate, filtered, and the filtrate is evaporated. The oily residue is admixed with 10 ml. of methanol, whereupon the product separates in crystalline form containing lattice-bound methanol. In this way 3.81 g. (85%) of 1-ethyl-1-(2'-methoxycarbonylethyl)-9-bromo-1,2,3,4,6,7-hexahydro-12H-indolo[2,3-a]quinolizin-5-ium methoxide are obtained; m.p.: 140°-142° C.

Workup

  1. customThe phases are separated
  2. customthe organic phase is dried over 10 g
  3. filtrationof solid anhydrous sodium sulfate, filtered
  4. customthe filtrate is evaporated to a final volume of about 40 ml
  5. additionof dry ferric chloride are added to this concentrate
  6. additionThe addition
  7. customin 5 minutes
  8. filtrationof 10% aqueous ammonia, and the precipitated ferric hydroxide is filtered off
  9. customThe organic phase of the filtrate is separated
  10. customdried over 10 g
  11. filtrationof solid anhydrous sodium sulfate, filtered
  12. customthe filtrate is evaporated
  13. additioncontaining lattice-bound methanol

Sources & evidence

ORD record
ord-8088b58d26484b6eaa4434411ada9ada
Source dataset
uspto-grants-1984_06
Patent number
US04456607

Reaction notes

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