Cyclopropylamine → N-[2-(biphenyl-4-yloxy)ethyl]cyclopropanamine

HRID 77692Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Br[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>O1CCCC1>[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][NH:4][CH:1]2[CH2:3][CH2:2]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 5.15 g (90.2 mmol) of cyclopropylamine and 2.5 ml (18.04 mmol) of thiethylamine in 50 ml of tetrahydrofurane is added 5 g (18.04 mmol) of 4-(2-bromoethoxy)biphenyl. The reaction mixture is heated at 50° C. for 5 hrs. The solvent and the excess of cyclopropylamine are then removed under vacuum and the residue is dissolved in ethyl acetate. The organic solution is acidified to pH=4 by adding a 1N solution of HCl. The abundant obtained white precipate is filtered, washed by water and to diisopropyl ether and dried under vacuum to yield 4.4 g (96% yield) of N-[2-(biphenyl-4-yloxy)ethyl]cyclo-propanamine as its hydrochloride salt. mp (melting point)=252° C.

Workup

customThe solvent and the excess of cyclopropylamine are then removed under vacuum
dissolutionthe residue is dissolved in ethyl acetate
additionby adding a 1N solution of HCl
filtrationThe abundant obtained white precipate is filtered
washwashed by water and to diisopropyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-1175b6f10b554d82a26c60984a667fef
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841332B2

Reaction notes

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