Diethylamine → HCID 19031009, compound

HRID 266814Notes

Reaction equation

HRID 266814 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-525c8489e03b445b839885d41f642316
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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