Triethylamine → HCID 21276268, compound

HRID 1381625Notes

Reaction equation

HRID 1381625 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O.[C:36]1([NH:42][CH2:43][CH2:44][NH2:45])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:45][CH2:44][CH2:43][NH:42][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:21])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 742701,2-Ethanediamine, N1-phenyl-HCID 139357676-{[2-(3,4-Dimethoxyphenyl)ethyl]amino}-6-oxohexanoic acid

Product 1

HCID 21276268HCID 21276268, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[2-(3,4-Dimethoxyphenyl)ethylamino]-6-oxohexanoic acid (6.0 g, 0.019) was dissolved in dry dichloromethane (200 ml) and triethylamine (2.28 g, 0.021 mole), and ethyl chloroformate (1.86 ml, 0.019 mole) added at 0°. After 1 hour at 0° N-phenyl-1,2-ethanediamine (2.64 g, 0.019 mole) was added and the mixture stirred at room temperature for 18 hr. After washing with water and drying (Na2SO4), the reaction mixture was evaporated and the residue recrystallised from ethyl acetate to give the sub title compound (5.3 g) mp 109°-11°.

Workup

  1. washAfter washing with water
  2. dry with materialdrying (Na2SO4)
  3. customthe reaction mixture was evaporated
  4. customthe residue recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-0c18f38fb8204b2ab159c3f146d83074
Source dataset
uspto-grants-1989_02
Patent number
US04803225

Reaction notes

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