(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonate → (+/-)-1-(Cyclohexylmethyl)-4-(oxiran-2-ylmethyl)piperazine

Reaction equation

[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:14]1[CH2:16][CH:15]1[CH2:17]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O>>[CH:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:17][CH:15]3[CH2:16][O:14]3)[CH2:12][CH2:13]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Reactant 2

HCID 286836(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonate

HCID 27358851-(Cyclohexylmethyl)piperazine

Product 1

HCID 86661984(+/-)-1-(Cyclohexylmethyl)-4-(oxiran-2-ylmethyl)piperazineYield 92%

Procedure

The same method as employed in the preparation of Intermediate 1 but starting from 1-cyclohexylmethyl piperazine and (±)-3-nitro-benzenesulfonic acid oxiranylmethyl ester gives after flash chromatography the title compound as a yellow oil in a 92% yield.

Sources & evidence

ORD record: ord-2b93a9fd214047b3ae7e3a165f7700a8
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053436B1

Reaction notes

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