Benzylethanolamine → HCID 14868771, compound

HRID 899143Notes

Reaction equation

HRID 899143 reaction equation
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[CH2:16]([NH:23][CH2:24][CH2:25]O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:16]([N:23]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:10])=[O:8])[CH2:24][CH2:25][O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 4348BenzylethanolamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531Diisopropylethylamine

Product 1

HCID 14868771HCID 14868771, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triflic anhydride (11.18 g, 6.5 ml, 39 mmol) dissolved in 90 ml of DCM was added drop by drop to a well stirred solution of N-benzyl ethanol amine (2 g, 13.2 mmol) and diisopropylethyl amine (5.1 g, 6.9 ml, 39.7 mmol) in dichloromethane (160 ml) at 0° C. and stirred at room temperature for 1 h under nitrogen atmosphere. The reaction mixture was quenched with water and extracted with dichloromethane. Organic layer was washed with water and dried under sodium sulfate. Solvent evaporation under reduced pressure afforded 500 mg of the title compound as a an oil

Workup

  1. additionwas added drop by drop to a well
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with dichloromethane
  4. washOrganic layer was washed with water
  5. customdried under sodium sulfate
  6. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-da886d6c070a4f09b3e601effffb3658
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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