Triethylamine → HCID 19848990, compound

HRID 1608268Notes

Reaction equation

HRID 1608268 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>ClCCl>[O:25]=[C:22]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 11535728Ethyl [4-(aminomethyl)phenyl]acetate

Product 1

HCID 19848990HCID 19848990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Ethyl 4-[aminomethyl]benzeneacetate (4.12 g) in anhydrous dichloromethane (60 ml) containing triethylamine (3.0 ml), was added over 20 min to a cold (-15°) stirred solution of acryloyl chloride (1.73 ml) in dry dichloromethane (50 ml) and stirring was continued for 0.75 h. After washing the dichloromethane solution with 8% aqueous sodium bicarbonate soln (2×50 ml) and drying (MgSO4), the organic solvent was removed by rotary evaporation to yield a a solid (approximately 6 g) which was triturated with cyclohexane to give the title compound as a solid (4.1 g) m.p. 93°-95°.

Workup

  1. additionwas added over 20 min to a cold (-15°)
  2. washAfter washing the dichloromethane solution with 8% aqueous sodium bicarbonate soln (2×50 ml)
  3. dry with materialdrying (MgSO4)
  4. customthe organic solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-9a6df62c80734d4b9d8c4d8bc3031825
Source dataset
uspto-grants-1989_09
Patent number
US04870096

Reaction notes

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