Dimethylformamide → HCID 22116806, compound

18.54 g (100 mmol) dodecylamine(laurylamine), 6.36 g (60 mmol) Na2CO3 and 50 mg tetrabutyl ammonium iodide (TBAI) were suspended in 100 ml anhydrous DMF in a 500 ml 3-neck flask having a reflux condenser and a dropping funnel. A solution of 16.4 ml (60 mmol) 1-bromo tetradecane in 100 ml anhydrous dioxane were added dropwise at 100° C. over a period of 110 minutes and the mixture was steered for another 3.5 hours at 100° C. (FIG. 6). The solution was filtered at a temperature as hot as possible. The crystalline solid which precipitated at 4° C. over night, was removed and was washed with a little of cold methanol. Subsequently, the solid was re-crystallised from 200 ml methanol. 9 g of colourless leaf-like crystals were obtained which are re-crystallised from 100 ml MtBE. The crystals which precipitated at −18° C., were sucked off from a cooled frit and washed with cold MtBE. 7.94 g (21 mmol) of a colourless crystalline solid were obtained, corresponding to a yield of 35%.

1. filtrationThe solution was filtered at a temperature as hot as possible
2. customThe crystalline solid which precipitated at 4° C. over night
3. customwas removed
4. washwas washed with a little of cold methanol
5. customSubsequently, the solid was re-crystallised from 200 ml methanol
6. custom9 g of colourless leaf-like crystals were obtained which
7. customare re-crystallised from 100 ml MtBE
8. customThe crystals which precipitated at −18° C.
9. washwashed with cold MtBE

ORD record

ord-afbf0fd0ac544d4fba2ecb6a193c8ee4

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357722B2