Ammonia → HCID 20455131, compound

HRID 2296247Notes

Reaction equation

HRID 2296247 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>[BrH:32].[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 20455131HCID 20455131, compoundYield 90%

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 and filtered. The filtrate is admixed with 50 ml. of glacial acetic acid, and dichloromethane is distilled off in vacuo. 0.67 ml. (13 mmoles, 2.08 g.) of elemental bromine are added dropwise, under vigorous stirring, to the residue at 25° C. The reaction mixture is stirred at room temperature for 3 hours, the precipitated yellow, crystalline product is filtered off and dried. In this way 4.5 g. of 1-ethyl-1-(2'-methoxycarbonylethyl)-9-bromo-1,2,3,4,6,7-hexahydro-12H-indolo[2,3-a]quinolizin-5-ium hydrobromide are obtained; yield: 90%, m.p.: 127°-128° C. The NMR spectrum of the product has the characteristic bands as indicated in Example 7.

Workup

  1. customThe phases are separated
  2. customthe organic phase is dried over 10 g
  3. filtrationof solid anhydrous sodium sulfate and filtered
  4. distillationof glacial acetic acid, and dichloromethane is distilled off in vacuo
  5. filtrationthe precipitated yellow, crystalline product is filtered off
  6. customdried

Sources & evidence

ORD record
ord-a834220e832e483d9196f217f7c4bebe
Source dataset
uspto-grants-1984_01
Patent number
US04428877

Reaction notes

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