Methanol → HCID 19030944, compound

HRID 266828Notes

Reaction equation

HRID 266828 reaction equation
[C:1]([CH2:4][CH2:5][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)([OH:3])=[O:2].S(Cl)(Cl)=O.[CH3:35]O>>[CH3:35][O:2][C:1]([CH2:4][CH2:5][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)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 19031147HCID 19031147, compound

Product 1

HCID 19030944HCID 19030944, compound

Procedure

1-{1-[4-(2-Carboxyethyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (2 g) is dissolved in methanol (50 ml) and thereto is added dropwise thionyl chloride (1.1 ml) under ice cooling. After adding, the mixture is stirred at 0°-5° C. for 1 hour and further at room temperature overnight. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) and recrystallized from n-hexane to give 1-{1-[4-(2-methoxycarbonylethyl)benzoyl]-4-piperidinyl}-3,4-dihyrocarbostyril (1.46 g) as white powder, m.p.: 85°-86° C.

Workup

  1. additionAfter adding
  2. concentrationThe solvent is concentrated
  3. customthe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)
  4. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-a545d52deafc415a97073cc5224b880a
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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