Triethylamine → HCID 18334081, compound

HRID 2269497Notes

Reaction equation

HRID 2269497 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:20]([NH2:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21].C(N(CC)CC)C.C([BH3-])#N.[Na+]>ClCCl.C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C.C(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:29][C:20]([CH3:22])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:21])=[CH:13][CH:14]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 794540(4-Methoxyphenyl)(3-nitrophenyl)methanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18334081HCID 18334081, compoundYield 38%

Reagents, catalysts & solvents 5

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2.57 g of 4-methoxyphenyl 3-nitrophenyl ketone, 1.35 g of cumyl amine and 1.35 g of triethylamine were dissolved in 50 ml of dichloromethane, and then 30 ml of a solution of 1.65 ml of titanium tetrachloride in dichloromethane was added dropwise whilst ice cooling. The reaction mixture was stirred at room temperature for 2 hours and was then heated under reflux for 3 hours. The reaction mixture was allowed to cool, after which it was diluted with 150 ml of ethyl acetate. The insoluble matter was then filtered off. The filtrate was washed with a saturated solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. Following a similar reaction, separation and purification procedure to that described in Example (1a), the resulting brown oil, 100 ml of ethanol 2.51 g of sodium cyanoborohydride and 2.58 ml of acetic acid were reacted, to obtain 1.43 g of the title compound as a yellow oil.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. filtrationThe insoluble matter was then filtered off
  5. washThe filtrate was washed with a saturated solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customa similar reaction, separation and purification procedure to

Sources & evidence

ORD record
ord-fbc68857273849b89ee276d2977c81e1
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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