Formaldehyde → 2-((Dimethylamino)methyl)cyclohexanone

To cyclohexanone (259 mL) was added formaldehyde (37.2 mL of a 37% aqueous solution) and dimethylamine hydrochloride (40.8 g). The stirred mixture was slowly heated and refluxed for 1 h. After cooling to ambient temperature H2O was added, and the mixture was extracted twice with Et2O. The aqueous layer was made basic by addition of 50% aqueous NaOH (27.5 mL), and subsequently extracted twice with DCM. The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to give 66.6 g of a light-yellow liquid. 1H NMR (400 MHz, CDCl3) δ 1.34-1.47 (m, 1H), 1.60-1.78 (m, 2H), 1.81-1.92 (m, 1H), 1.98-2.09 (m, 1H), 2.16-2.55 (m, 5H), 2.21 (s, 6H), 2.69 (dd, J=13 and 6 Hz, 1H).

1. temperatureThe stirred mixture was slowly heated
2. temperaturerefluxed for 1 h
3. additionwas added
4. extractionthe mixture was extracted twice with Et2O
5. additionThe aqueous layer was made basic by addition of 50% aqueous NaOH (27.5 mL)
6. extractionsubsequently extracted twice with DCM
7. dry with materialThe combined organic phases were dried over Na2SO4
8. customevaporated under reduced pressure

ORD record

ord-e0efabadef9048dc84919e5833e7dc29

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728018B2