2-Bromoethyldiethylammonium bromide → HCID 57987616, compound

To methyl cyclopentanecarboxylate (1 g) in THF (8 ml) at −61° C. is added a solution of 2M LDA (9.8 ml). The mixture is stirred at room temperature for 15 minutes, then 2-bromo-N,N-diethylethanamine hydrobromide (2.04 g) is added at −61° C. The mixture is stirred for 5 minutes at this temperature, then at room temperature. The solution became yellow and was diluted with water (30 ml). The organic phase is extracted twice with a brine solution (30 ml). The pH of the organic phase is adjusted to 4 with 6N HCl. After decantation, the aqueous phase is extracted with CH2Cl2 (20 ml) and the pH of aqueous phase adjusted to 12 with 6 N NaOH. After decantation, the organic phase is dried over MgSO4 and concentrated. The residue is treated with diethyl ether (10 ml) and the white solid is filtrated. Methyl 1-[2-(diethylamino)ethyl]cyclopentanecarboxylate 280 is obtained as a yellow liquid after concentration of the ether solution.

1. stirringThe mixture is stirred for 5 minutes at this temperature
2. customat room temperature
3. extractionThe organic phase is extracted twice with a brine solution (30 ml)
4. extractionAfter decantation, the aqueous phase is extracted with CH2Cl2 (20 ml)
5. dry with materialAfter decantation, the organic phase is dried over MgSO4
6. concentrationconcentrated
7. additionThe residue is treated with diethyl ether (10 ml)
8. filtrationthe white solid is filtrated

ORD record

ord-fc702576ba9f4e9ab4c95441bc0e65c5

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07638630B2