3-Chlorobenzaldehyde → HCID 86758785, compound

HRID 1634036Notes

Reaction equation

HRID 1634036 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:11](=[O:22])[CH2:10][S:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=[C:10]1[S:9][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:12]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:11]1=[O:22]

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 12050574HCID 12050574, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86758785HCID 86758785, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

2-( 3-Chlorophenyl)-3-(3-piperidin-1-ylpropyl)-thiazolidin-4-one (3 mm, 1 g), 3-chlorobenzaldehyde (4.5 mm, 0.51 mL), and potassium t-butoxide (4.5 mm, 0.5 g) are mixed in 50 mL toluene with molecular sieves and heated at 60° C. for 4 hours. The molecular sieves are removed by filtration, and the solvent is concentrated to dryness. Pure Compound 2 (0.5 g) is isolated by column chromatography (5% MeOH/CH2Cl2). MS: m/z (APCI, AP+) 462 [M]+. MP 137-139° C.

Workup

  1. customThe molecular sieves are removed by filtration
  2. concentrationthe solvent is concentrated to dryness

Sources & evidence

ORD record
ord-ccd59367589447a5a56c08f6ca88bc93
Source dataset
uspto-grants-2003_01
Patent number
US06506751B1

Reaction notes

Loading…