Hydrochloric Acid → HCID 178448597, compound

HRID 2206445Notes

Reaction equation

HRID 2206445 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C=O.Cl.[CH2:9](O)C.[CH2:12]([N:14]([CH2:29][CH3:30])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=O)=[CH:17][CH:16]=1)[CH3:13].[C:31]1([B-:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Na+]>C(#N)C.CO>[C:50]1([B-:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1.[CH2:1]([N:5]1[C:21]([C:18]2[CH:19]=[CH:20][C:15]([N:14]([CH2:29][CH3:30])[CH2:12][CH3:13])=[CH:16][CH:17]=2)=[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N+:24]2=[CH:9]1)[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 712FormaldehydeHCID 8007ButylamineHCID 2723787Sodium TetraphenylborateHCID 86732005HCID 86732005, compound

Product 1

HCID 178448597HCID 178448597, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

was prepared according to general procedure (A), in which 25 μl n-butylamine (0.21 mmol, 1 equiv), 24 μl formalin (0.32 mmol, 1.5 equiv), 0.14 mL 3.05 M hydrochloric acid in ethanol (0.43 mmol, 2 equiv) and 54 mg (4-(diethylamino)phenyl)(pyridin-2-yl)methanone (0.21 mmol, 1 equiv) were combined in 1.0 mL acetonitrile and maintained at room temperature for 12 hours. The reaction was concentrated in vacuo and dried under high vacuum at 0.2 Torr. The resulting crude material was dissolved in 1.5 mL ethanol and stirred with 0.8 g sodium bicarbonate for 1 hour at room temperature. The resulting suspension was then filtered through a 0.2 um nylon syringe tip filter, washed with ethanol three times using 6 mL of ethanol for each wash and filtered. The combined filtrate was concentrated. The resulting crude oil was dissolved in 1.5 mL methanol and 73 mg sodium tetraphenylborate (0.21 mmol, 1 equiv) in 1.5 mL methanol was added drop wise to the oil while stirring vigorously. The heterogeneous mixture was stirred vigorously for 3 hours at room temperature until the solid became a fine suspension. The mixture was cooled to 4° C. in a refrigerator. The solid was then filtered, rinsed with methanol three times using 0.25 mL of methanol for each rinse and dried under high vacuum at 0.2 Torr to obtain 96 mg 2-butyl-1-(4-(diethylamino)phenyl)-2H-imidazo[1,5-a]pyridin-4-ium tetraphenylborate (0.15 mmol, a 70% yield) as an orange solid.

Workup

  1. customwas prepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customdried under high vacuum at 0.2 Torr
  4. dissolutionThe resulting crude material was dissolved in 1.5 mL ethanol
  5. filtrationThe resulting suspension was then filtered through a 0.2 um nylon syringe tip
  6. filtrationfilter
  7. washwashed with ethanol three times
  8. washeach wash
  9. filtrationfiltered
  10. concentrationThe combined filtrate was concentrated
  11. dissolutionThe resulting crude oil was dissolved in 1.5 mL methanol
  12. stirringwhile stirring vigorously
  13. stirringThe heterogeneous mixture was stirred vigorously for 3 hours at room temperature until the solid
  14. temperatureThe mixture was cooled to 4° C. in a refrigerator
  15. filtrationThe solid was then filtered
  16. washrinsed with methanol three times
  17. washeach rinse
  18. customdried under high vacuum at 0.2 Torr

Sources & evidence

ORD record
ord-2519a549d9644b519279ea6f2cb20c15
Source dataset
uspto-grants-2016_06
Patent number
US09371448B2

Reaction notes

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