Hydrochloric Acid → HCID 86743853, compound

HRID 704837Notes

Reaction equation

HRID 704837 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[N:11]1)[CH3:2].B#B.Cl.[OH-].[Na+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>C1COCC1.C(O)C>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[CH2:27]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:12]=[N:11]1)[CH3:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 6328200Diboron2×HCID 14699560HCID 14699560, compound

Product 1

HCID 86743853HCID 86743853, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 11.5 g (0.029 mol) of N-[3-(diethylamino)propyl]-4,5-diphenyl-1H-pyrazole-1-ethanamine of example 12 in 160 mL of THF was added dropwise with stirring at 0° C. under nitrogen to 240 mL of a 1M THF solution of diborane (0.024 mol). The reaction was slowly heated to reflux and allowed to reflux 18 hr. The solvent and excess diborane were stripped off in vacuo, and the residue was treated with 400 mL of 6N HCl, cautiously at first, then with heating on steambath for 1 hr. The solution was cooled, made basic with NaOH, and extracted into methylene chloride; the methylene chloride solution was dried over MgSO4 and stripped to a dark oil. The oil was dissolved in hot ethanol and a solution of 2 equivalents of fumaric acid in hot ethanol was added. The solution was chilled and 8.7 g of N-[3-(diethylamino)propyl]-4,5-diphenyl-1H-pyrazole-1-ethanamine (E)-2-butenedioate (1:2), mp 95°-100° C., was obtained by filtration.

Workup

  1. temperatureThe reaction was slowly heated
  2. temperatureto reflux
  3. temperatureto reflux 18 hr
  4. temperaturecautiously at first, then with heating on steambath for 1 hr
  5. temperatureThe solution was cooled
  6. extractionextracted into methylene chloride
  7. dry with materialthe methylene chloride solution was dried over MgSO4
  8. dissolutionThe oil was dissolved in hot ethanol
  9. temperatureThe solution was chilled

Sources & evidence

ORD record
ord-9dc729f951da4aa5b89d059aca9126b5
Source dataset
uspto-grants-1991_01
Patent number
US04988725

Reaction notes

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