Benzylethanolamine → HCID 69072061, compound

HRID 899158Notes

Reaction equation

HRID 899158 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[CH2:7]([NH:14][CH2:15][CH2:16][OH:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([N:14]([CH2:15][CH2:16][OH:17])[C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 4348BenzylethanolamineHCID 6598Dimethylcarbamoyl ChlorideHCID 8471Triethylamine

Product 1

HCID 69072061HCID 69072061, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-dimethyl carbamoyl chloride (2.55 g, 0.0238 mol) was added drop by drop at 0° C. to a solution of N-benzyl ethanol amine (3 g, 0.0198 mol) and triethylamine (3 g, 0.0298 mol) in 25 ml of DCM (dry) and stirred at RT for 3 h under nitrogen atmosphere. The reaction was quenched with water, extracted with dichloromethane, washed with water, brine and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by column chromatography over silica gel using 3.5% methanol in dichloromethane as eluent afforded 4 g of the sub-title compound as a liquid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-c55a788bef7447a3986b8639b3f27236
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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