Benzylamine → 1-Benzyl-2,5-dihydropyrrole

HRID 1018048

Reaction equation

C(O)/C=C\CO.[CH2:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH3:8].CS(Cl)(=O)=O.C(N)[C:20]1[CH:25]=[CH:24]C=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH2:7]([N:9]1[CH2:12][CH:13]=[CH:11][CH2:10]1)[C:8]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution containing 35.4 g (0.4 mol) of cis-2-butene-1,4-diol, 83.8 g (0.8 mol) of triethylamine, and 416.6 g of ethyl acetate in a round flask reactor, methanesulfonyl chloride was added dropwise with stirring for 30 min. at about 5° C. using an ice-bath. After addition, the mixture was allowed to react with stirring for 2 hours at room temperature. To the mixture, 171.7 g (1.6 mol) of benzylamine was added continuously dropwise with stirring for 30 min. at ambient temperature. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 52.2 g of 1-benzyl-3-pyrroline (yield 82.0%) was obtained.

Workup

additionAfter addition
customto react
stirringwith stirring for 2 hours at room temperature
stirringwith stirring for 30 min. at ambient temperature
stirringAfter 2 hours of stirring
customthe crystallized solid was removed by filtration
addition42.0 g of 35% HCl (aq) was added to the filtrate
customexcess benzylamine hydrochloride was removed by filtration or extraction
customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-70e69831df4f44189c995d7bf82f4324
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479668B1

Linked notes

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