Trifluoroacetic acid → 2-[2-(6-Chlorohexyloxy)ethoxy]ethylammonium trifluoroacetate

HRID 1397968Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C.[F:22][C:23]([F:28])([F:27])[C:24]([OH:26])=[O:25].ClCCl.CO>ClCCl>[F:22][C:23]([F:28])([F:27])[C:24]([O-:26])=[O:25].[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][NH3+:14]

Participants

Conditions

Temperature: 0 °C

Procedure

Under argon atmosphere, to a solution of tert-butyl N-[2-{2-(6-chlorohexyloxy)ethoxy}ethyl]carbamate (11) (synthesized by the method described in Non-Patent Document Y. Zhang, M.-k. So, A. M. Loening, H. Yao, S. S. Gambhir, J. Rao, Angew. Chem. Int. Ed., 2006, 118, 4936-4940) (84.2 mg, 260 pump in dichloromethane (2.5 mL) was added trifluoroacetic acid (0.5 mL) at 0° C. After stirring for 2 hours at the same temperature of 0° C., the starting compound 11 completely disappeared as judged from TLC study (Rf=0.41, dichloromethane/methanol=9/1). The reaction solution was then concentrated under reduced pressure using an evaporator to give crude 2-[2-(6-chloro hexyloxy)ethoxy]ethylammonium trifluoroacetate (12) as a colorless oil. The crude product was used in the next reaction without further purification.

Workup

concentrationThe reaction solution was then concentrated under reduced pressure
customan evaporator

Sources & evidence

ORD record: ord-5ded7405e92c4027b150a23d4a9306c5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901312B2

Reaction notes

Loading…