Ethylamine → HCID 10619896, compound

HRID 1531870Notes

Reaction equation

HRID 1531870 reaction equation
[C:1]1(=[O:26])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.[CH2:27]([NH2:29])[CH3:28]>>[CH2:27]([NH:29][C:8](=[O:9])[CH2:7][CH:6]([N:5]1[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]2[C:1]1=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH3:28]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 103608253-(3,4-Dimethoxyphenyl)-3-phthalimidopropanoic acid

Product 1

HCID 10619896HCID 10619896, compoundYield 77%

Procedure

The procedure of Example 46 was followed utilizing 3-phthalimido-3-(3,4-dimethoxyphenyl)propionic acid and ethylamine (1.0 equiv). After the reaction mixture was concentrated, the residue was diluted with 20 mL of water and 1 mL of ether. The mixture was stirred for 1 hour to afford a slurry. The slurry was filtered and the solid dried in vacuo to afford 0.66 g (77%) of 3-phthalimido-3-(3,4-dimethoxyphenyl)propionic ethylamide compound as a white powder: mp 131.0-132.5° C.; 1H NMR (DMSO-d6, 250 MHz) δ8.08 (t, 1H, J=5 Hz), 7.78-7.95 (m, 4H), 7.03 (s, 1H), 6.85-7.00 (m, 2H), 5.69 (t, 1H, J=8 Hz), 3.74 (s, 3H), 3.72 (s, 3H), 3.18 (d, 2H, J=8 Hz), 2.98(m, 2H), 0.88 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ168.8, 167.7, 148.5, 148.2, 134.5, 131.6, 131.2, 123.1, 119.4, 111.6, 111.1, 55.5, 50.5, 37.3, 33.2, 14.5; Anal. Calcd. for C21H22N2O5. Theoretical: C, 65.96; H, 5.80; N, 7.33. Found: C, 65.85; H, 5.84; N, 7.24.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. additionthe residue was diluted with 20 mL of water and 1 mL of ether
  3. customto afford a slurry
  4. filtrationThe slurry was filtered
  5. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-eaf5ed9a07174ba7a8fae7520f3ce205
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

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