Triethylamine → HCID 22675353, compound

HRID 1006072Notes

Reaction equation

HRID 1006072 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][NH2:14])[CH2:7][CH2:6]1.Br[CH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=1[C:25](OC)=[O:26].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:22][C:23]3[C:24](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:25]2=[O:26])[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 22675369HCID 22675369, compound

Product 1

HCID 22675353HCID 22675353, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution (5 ml) of 3-[4-(2-bromo-5-methoxybenzyl)-1-piperidinyl]propylamine (400.0 mg, 1.179 mmol), methyl 2-(bromomethyl)benzoate (400.0 mg, 1.746 mmol) and triethylamine (200.0 mg, 1.976 mmol) in toluene was stirred with heating under reflux for 5 hours. The reaction solution was diluted with ethyl acetate and the triethylamine hydrobromide produced during the reaction was filtered off. Then, the solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (hexane/ethyl acetate=3/1˜ethyl acetate˜triethylamine/ethyl acetate=1/19) to obtain the title compound (439.3 mg, 0.960 mmol) in a yield of 82%.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 5 hours

Sources & evidence

ORD record
ord-a272cf2a208842e8aef64098b4e8348d
Source dataset
uspto-grants-2004_09
Patent number
US06787560B2

Reaction notes

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