Benzyl Bromide → HCID 14772399, compound

HRID 2073711Notes

Reaction equation

[N:1]1[O:2][C:3]2[CH2:4][CH2:5][CH2:6][CH:7]3[C:16]=2[C:15]=1[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:8]3.C([O-])([O-])=O.[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([N:8]1[CH:7]2[C:16]3=[C:3]([O:2][N:1]=[C:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=3)[CH2:4][CH2:5][CH2:6]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In 50 ml dry DMF were combined 2.10 g 4,5,5a,6-tetrahydro-3H-isoxazolo[5,4,3-kl]acridine, 2.0 g milled anhydrous K2CO3 and 1.3 ml benzylbromide. The mechanically stirred mixture was heated under nitrogen at 90° C. for 18 hours. During the first 4 hours, 1 ml benzyl bromide was added every hour as TLC analysis indicated it was being consumed. For the work-up, the mixture was poured in excess water and extracted with DCM. The DCM layer was concentrated to an oil and the oil was purified on a silica column (flash chromatography) using DCM as an eluent. The product-containing fractions were combined and concentrated to a solid. The solid was recrystallized from EtOAc/hexanes and dried in a vacuum desiccator to yield 2.10 g of product, m.p. 162°-163.5° C.

Workup

customwas being consumed
additionFor the work-up, the mixture was poured in excess water
extractionextracted with DCM
concentrationThe DCM layer was concentrated to an oil
customthe oil was purified on a silica column (flash chromatography)
concentrationconcentrated to a solid
customThe solid was recrystallized from EtOAc/hexanes
customdried in a vacuum desiccator

Sources & evidence

ORD record: ord-9f7595fbcf804089b9e384cad0000205
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04920117

Reaction notes

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