Benzylethanolamine → HCID 86606266, compound

HRID 1823256Notes

Reaction equation

HRID 1823256 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S(O)(=O)=O)C=CC=CC=1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38]>C(Cl)Cl.CCOC(C)=O>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[CH2:1]([NH:8][CH2:9][CH2:10][O:11][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][O:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 4348BenzylethanolamineHCID 7371Benzenesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 444266Maleic Acid

Product 1

HCID 86606266HCID 86606266, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

100 g of 2-(benzylamino)-1-ethanol are added at ambient temperature to a mixture of 110 g of benzenesulfonic acid in 1.8 liters of DCM, the temperature at the end of the addition being 34.4° C. and the pH=2. The reaction mixture is cooled to 20° C. and 105 ml of 3,4-dihydro-2H-pyran are added dropwise, the reaction mixture turning yellow, then pink and finally purple in color at the end of the addition. The mixture is poured onto 2 liters of a 10% aqueous K2CO3 solution, then, after separating by settling, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. The oil obtained is dissolved in 200 ml of AcOEt, a hot solution of 72.7 g of maleic acid in 655 ml of AcOEt is added and the mixture is left stirring overnight at ambient temperature. The precipitate formed is filtered off, washed with 3×100 ml of AcOEt and dried under vacuum at ambient temperature. 207 g of the expected product are obtained in the maleate form.

Workup

  1. additionthe temperature at the end of the addition
  2. custombeing 34.4° C.
  3. additionpink and finally purple in color at the end of the addition
  4. customafter separating
  5. dry with materialthe organic phase is dried over Na2SO4
  6. customthe solvent is evaporated under vacuum
  7. customThe oil obtained
  8. waitthe mixture is left
  9. customThe precipitate formed
  10. filtrationis filtered off
  11. washwashed with 3×100 ml of AcOEt
  12. customdried under vacuum at ambient temperature

Sources & evidence

ORD record
ord-9f2dc2b667fa4bd2abb605d262865e40
Source dataset
uspto-grants-2006_05
Patent number
US07038044B1

Reaction notes

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