4-Toluenesulfonyl chloride → trans-N-p-Tolylsulfonyl-1,2-diaminocyclohexane

HRID 2217092Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[NH2:8])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -7.5 °C

Procedure

To a stirred solution of (R,R)-1,2-diaminocyclohexane (300 g, 2.63 mole) in CH2Cl2 (5.00 l) at −10° C. was added a solution of p-toluenesulfonylchloride (209 g, 1.10 mole) in CH2Cl2 (5.00 l) dropwise over a 7 h period, maintaining the temp at −5 to −10° C. The mixture was allowed to warm to room temp while stirring overnight. The mixture was concentrated in vacuo to a volume of 3 l and the white solid was removed by filtration. The solution was then washed with H2O (10×1 l) and was dried over MgSO4. Removal of the solvent in vacuo gave 286 g (97.5% yield) of the product as a yellow crystalline solid: 1H NMR (CDCl3) δ 0.98-1.27 (m, 4H), 1.54-1.66 (m, 2H), 1.81-1.93 (m, 2H), 2.34 (dt, J=4.0, 10.7 Hz, 1H), 2.42 (s, 3H), 2.62 (dt, J=4.2, 9.9 Hz, 1H), 7.29 (d, J=8.1 Hz, 2H), 7.77 (d, J=8.3 Hz, 2H); MS (LRFAB-DTT-DTE) m/z 269 [M+H]+.

Workup

temperatureto warm to room temp
concentrationThe mixture was concentrated in vacuo to a volume of 3 l
customthe white solid was removed by filtration
washThe solution was then washed with H2O (10×1 l)
dry with materialwas dried over MgSO4
customRemoval of the solvent in vacuo

Sources & evidence

ORD record: ord-dd8fbb91771a43d5bb41599a61aa7f42
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407645B2

Reaction notes

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