Potassium Carbonate → HCID 69100293, compound

HRID 2115147Notes

Reaction equation

HRID 2115147 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:18])[CH:15](Br)[CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:29]=[CH:28][C:23]2[NH:24][C:25](=[O:27])[O:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:18])[CH:15]([NH:19][C:20]2[CH:29]=[CH:28][C:23]3[NH:24][C:25](=[O:27])[O:26][C:22]=3[CH:21]=2)[CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8269896-amino-1,3-benzoxazol-2(3H)-oneHCID 52984034HCID 52984034, compound

Product 1

HCID 69100293HCID 69100293, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.03 g (3.33 mmol) of 1-(4-benzyl-piperidine-1-yl)-2-bromo-propan-1-one, 0.5 g (3.33 mmol) of 6-amino-3H-benzoxazol-2-one, 1.0 g (7.2 mmol) of potassium carbonate and 15 ml of dimethylformamide is refluxed for 5 hours. The reaction mixture is filtered and the filtrate is concentrated. The residue is purified by column chromatography using Kieselgel 60 adsorbent (Merck) and hexane:ethyl acetate=4:1 as eluent to yield 0.46 g (36.5%) of the title compound. Melting Point: 91° C. (hexane)

Workup

  1. temperatureis refluxed for 5 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-38ba5308c11841419c38938a39e0815d
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

Loading…