Triethylamine → HCID 86651470, compound

HRID 1875486Notes

Reaction equation

HRID 1875486 reaction equation
[C:1]([O-])(=O)C.[CH3:5][C:6]1[C:15]([CH3:17])([CH3:16])[C:14]2[C:9]3=[C:10]([CH2:18][CH2:19][NH+:8]3[CH:7]=1)[CH:11]=[CH:12][CH:13]=2.C1(N[CH:27]=[N:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)C=CC=CC=1.[Cl-:35].[OH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]1(C)[C:52]2[C:47]3=C(CC[NH+]3C=[C:44]1C)C=[CH:50][CH:51]=2.C(N(CC)CC)C>C(OC(=O)C)(=O)C.C(O)(=O)C.C(#N)C>[Cl-:35].[CH3:16][C:15]1([CH3:17])[C:14]2=[C:9]3[C:10](=[CH:11][CH:12]=[CH:13]2)[CH2:18][CH2:19][CH2:7][N:8]3/[C:6]/1=[CH:5]/[CH:50]=[CH:51]/[C:52]1[C:43]([CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][OH:36])([CH3:44])[C:30]2[C:29]3=[C:34]([CH2:1][CH2:27][NH+:28]3[CH:47]=1)[CH:33]=[CH:32][CH:31]=2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 94888N,N'-DiphenylformamidineHCID 67033780HCID 67033780, compoundHCID 67033784HCID 67033784, compound

Product 1

HCID 86651470HCID 86651470, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 7918Acetic AnhydrideSolvent2×

Procedure

A mixture of 5,6,6-trimethyl-1,2,3,6-tetrahydropyrrolo[3,2,1-ij]quinolinium acetate (1.0 g, 3.19 mmol) and N,N′-diphenylformamidine (939.6 mg, 4.79 mmol) in 10 mL acetic anhydride and 10 mL acetic acid were refluxed for 2 hours. After cooling to room temperature the volatiles were removed under reduced pressure. The resulting oil was diluted with CH2Cl2, washed with 2M HCl (aqueous), dried over Na2SO4 and concreted to give a brown solid. This solid was combined with 6-(6-hydroxyhexyl)-5,6-dimethyl-1,2,3,6-tetrahydropyrrolo[3,2,1-ij]quinolinium chloride (1.13 g, 3.51 mmol) in 15 mL acetic anhydride. To this stirring mixture was added 2.5 mL triethylamine. The reaction was heated to 90° C. for 1 hour yielding a dark mixture. After cooling to room temperature the volatiles were removed under reduced pressure. The residue was dissolved in CH2Cl2 and was washed with 2 M HCl. The separated organic phase was dried over Na2SO4 and concentrated to give a red solid. This was subsequently dissolved in 75 mL ACN/75 mL 1 M HCl (aqueous) and refluxed for 2.5 hours. The volume of the mixture was reduced to about 50 mL and the product was extracted with CH2Cl2. Evaporation of solvent gave a dark solid that was subjected to silica gel chromatography affording the product as a red solid. MS m/z calculated for C34H43N2O (M+): 495.3. Found 495.5 (M+, ESI+).

Workup

  1. temperaturewere refluxed for 2 hours
  2. customwere removed under reduced pressure
  3. additionThe resulting oil was diluted with CH2Cl2
  4. washwashed with 2M HCl (aqueous)
  5. dry with materialdried over Na2SO4
  6. customto give a brown solid
  7. temperatureThe reaction was heated to 90° C. for 1 hour
  8. customyielding a dark mixture
  9. temperatureAfter cooling to room temperature the volatiles
  10. customwere removed under reduced pressure
  11. dissolutionThe residue was dissolved in CH2Cl2
  12. washwas washed with 2 M HCl
  13. dry with materialThe separated organic phase was dried over Na2SO4
  14. concentrationconcentrated
  15. customto give a red solid
  16. temperaturerefluxed for 2.5 hours
  17. extractionthe product was extracted with CH2Cl2
  18. customEvaporation of solvent
  19. customgave a dark solid

Sources & evidence

ORD record
ord-abc98855c23e4a59967ee02bc04b8c1f
Source dataset
uspto-grants-2012_11
Patent number
US08309059B2

Reaction notes

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