Triethylamine → HCID 87244677, compound

HRID 1875483Notes

Reaction equation

HRID 1875483 reaction equation
[C:1]([O-])(=O)[CH3:2].C[C:6]1[C:15](C)(C)[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.[ClH:20].[C:21]1(N=CCC=NC2C=CC=CC=2)[CH:26]=CC=C[CH:22]=1.[Cl-].[OH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]1([CH3:59])[C:55]2[C:50]3=[C:51]([CH2:56][CH2:57][NH+:49]3[CH:48]=[C:47]1[CH3:58])[CH:52]=[CH:53][CH:54]=2.[CH2:60](N(CC)CC)C>C(OC(=O)C)(=O)C.C(O)(=O)C.C(#N)C.Cl>[Cl-:20].[CH3:60][C:1]1([CH3:2])[C:10]2=[C:9]3[C:14](=[CH:13][CH:12]=[CH:11]2)[CH2:15][CH2:6][CH2:7][N:8]3/[C:19]/1=[CH:18]/[CH:22]=[CH:21]/[CH:26]=[CH:58]/[C:47]1[C:46]([CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][OH:39])([CH3:59])[C:55]2[C:50]3=[C:51]([CH2:56][CH2:57][NH+:49]3[CH:48]=1)[CH:52]=[CH:53][CH:54]=2

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 12213307Malonaldehyde bis(phenylimine) monohydrochlorideHCID 67033780HCID 67033780, compoundHCID 67033784HCID 67033784, compound

Product 1

HCID 87244677HCID 87244677, compoundYield 73.7%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolventHCID 7918Acetic AnhydrideSolvent2×

Procedure

A mixture of 5,6,6-trimethyl-1,2,3,6-tetrahydropyrrolo[3,2,1-ij]quinolinium acetate (1.35 g, 6.29 mmol) and malonaldehyde bis(phenylimine)monohydrochloride (1.63 g, 6.29 mmol) in 10 mL acetic anhydride and 10 mL acetic acid were refluxed for 2 hours. The reaction mixture was then cooled to room temperature at which point 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 that was combined with 6-(6-hydroxyhexyl)-5,6-dimethyl-1,2,3,6-tetrahydropyrrolo[3,2,1-ij]quinolinium chloride (1.84 g, 5.73 mmol) in 20 mL acetic anhydride. To this stirring solution was added 5 mL triethylamine. The reaction was heated to 90° C. for 1 hour and then cooled to room temperature. The volatiles were concentrated under reduced pressure to give a dark oil. This oil was refluxed for 3 hours in 70 mL ACN and 70 mL 1 M HCl. The reaction mixture was concentrated to 50 mL and extracted with CH2Cl2. The separated organic phase was dried over Na2SO4 and concentrated to give a blue solid that was purified by silica gel flash chromatography affording the product (2.14 g, 73.7%) as a black solid. 1H-NMR (300 MHz, d6DMSO): δ 8.34 (m, 2H), 7.15 (m, 6H), 6.48 (t, 2H), 6.61 (m, 2H), 4.00 (s, 4H), 3.32 (m, 9H), 2.81 (s, 4H), 2.10 (m, 4H), 1.67 (s, 9H), 1.11 (m, 4H) ppm; MS m/z calculated for C36H45N2O2 (M+): 521.4. Found 521.5 (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 that
  7. temperatureThe reaction was heated to 90° C. for 1 hour
  8. temperaturecooled to room temperature
  9. concentrationThe volatiles were concentrated under reduced pressure
  10. customto give a dark oil
  11. concentrationThe reaction mixture was concentrated to 50 mL
  12. extractionextracted with CH2Cl2
  13. dry with materialThe separated organic phase was dried over Na2SO4
  14. concentrationconcentrated
  15. customto give a blue solid that
  16. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-61daae70fd004536bb99425fb2550298
Source dataset
uspto-grants-2012_11
Patent number
US08309059B2

Reaction notes

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