Diethylamine → HCID 19031009, compound

HRID 1648576Notes

Reaction equation

HRID 1648576 reaction equation
[CH2:1]([O:5][C:6]1[CH:30]=[CH:29][C:9]([C:10]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21][C:19]3=[O:20])[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[CH2:31]([NH:33][CH2:34][CH3:35])[CH3:32]>CO>[CH2:31]([N:33]([CH2:34][CH3:35])[CH2:3][CH:2]([OH:4])[CH2:1][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21][C:19]3=[O:20])[CH2:14][CH2:13]2)=[O:11])=[CH:29][CH:30]=1)[CH3:32]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 19031238HCID 19031238, compound

Product 1

HCID 19031009HCID 19031009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(4-Glycidoxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (200 mg) is dissolved in methanol (4 ml) and thereto is added diethylamine (0.26 ml) and the mixture is stirred at room temperature overnight, and then refluxed with heating for 3 hours. The solvent is concentrated and the residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1→dichloromethane:methanol=10:1) to give 1-{1-[4-(3-diethylamino-2-hydroxypropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.18 g)

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 3 hours
  3. concentrationThe solvent is concentrated
  4. customthe residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1→dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-75e69f06447d480880c40057b23b70f3
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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