Propylamine → HCID 16736832, compound

HRID 1170456Notes

Reaction equation

HRID 1170456 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([CH:6]1[C:11](=[O:12])OC(C)(C)OC1=O)=[O:5].[CH2:20]([NH2:23])[CH2:21][CH3:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4](=[O:5])[CH2:6][C:11]([NH:23][CH2:20][CH2:21][CH3:22])=[O:12]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 167368235-(2-Chlorobenzoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 16736832HCID 16736832, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 5-(2-chlorobenzoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.06 g, 7.30 mmol) in 100 mL of toluene was treated with neat propylamine (550 μL, 395 mg, 6.70 mmol) added dropwise via syringe. The reaction was then heated at 80-90° C. for 4 h. Once at rt, the reaction was concentrated to dryness. The residue was adsorbed onto flash silica gel and added to 19 cm of flash silica gel in a 5 cm dia. column. Elution with 4:1 hexanes/EtOAc afforded 851 mg (53%) of the title compound as a yellow oil.

Workup

  1. additionadded dropwise via syringe
  2. concentrationOnce at rt, the reaction was concentrated to dryness
  3. additionadded to 19 cm of flash silica gel in a 5 cm dia
  4. washElution with 4:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-b2cb57c9322748b48feb004e725fc5fc
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

Loading…