3-Phenylpropylamine → N-benzyl-N-ethyl-2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide

HRID 874198Notes

Reaction equation

HRID 874198 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]3[C:17]=2[CH2:18][C:19]([OH:21])=O)=[CH:4][CH:3]=1.[CH2:22](CCN)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:32][CH2:33][N:34]=C=NCCCN(C)C.Cl>ClCCl>[CH2:22]([N:34]([CH2:33][CH3:32])[C:19](=[O:21])[CH2:18][C:17]1[N:11]2[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]2=[N:9][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 162593-PhenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 185457132-(4-Chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid

Product 1

HCID 56592851N-benzyl-N-ethyl-2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamideYield 39.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.9 g (0.003 mol) of 2-(4-chlorophenyl)-7-methylimidazo[1,2-a]-pyridine-3-acetic acid and 0.6 g (0.0045 mol) of N-benzylethylamine were weighed, added to 80 mL of dry dichloromethane, then added with 1.0 g (0.005 mol) of EDC hydrochloride. Stirred at room temperature and reacted for 24 h, stopped the reaction until almost completion of the reaction. Filtered to remove solid urea, concentrated, and then separated with silica gel column chromatograph to obtain a crude product which was recrystallized with acetone to obtain a pure white solid powder, 0.5 g in total, yield 39.9%. m.p. 192-193° C., ESI-MS m/z: 419[M+H]+, 1H NMR (CDCl3, 400 MHz)δ: 1.20(t, 3H, J=7.00 Hz), 2.54(s, 1.7H), 2.56(s, 1.3H), 3.38(q, 0.8H, J=7.00 Hz), 3.57(q, 1.2H, J=7.00 Hz), 4.11(s, 1H), 4.21(s, 1H), 4.59(s, 0.7H), 4.62(s, 1.3H), 7.09-7.15(m, 2H), 7.24-7.37(m, 5H), 7.46-7.56(m, 2H), 7.69-7.71(m, 1H), 8.09-8.23(m, 2H).

Workup

  1. customreacted for 24 h
  2. customthe reaction
  3. customuntil almost completion of the reaction
  4. filtrationFiltered
  5. customto remove solid urea
  6. concentrationconcentrated
  7. customseparated with silica gel column chromatograph

Sources & evidence

ORD record
ord-6f26005015a44186b33ad8e83a4c18ed
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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