Iodoethane → HCID 86681545, compound

HRID 709015Notes

Reaction equation

[CH:1]1([NH:7][CH2:8][CH:9]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:26](I)[CH3:27]>ClCCCl>[C:12]([O:11][CH:9]([CH3:10])[CH2:8][N:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:26][CH3:27])(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of benzoic acid 2-cyclohexylamino-1-methyl-ethyl ester (1.0 g, 3.8 mmol) in DCE (20 mL) were added successively K2CO3 (2.11 g, 15.2 mmol) and ethyl iodide (1.8 mL, 22 mmol). The resulting mixture was heated at 50° C. for 16 hours in a sealed tube. Ethyl iodide (1.8 mL) was again added and the reaction mixture heated at 60° C. for another 24 hours. The reaction mixture was filtered and washed 5% methanol-DCM. The filtrate was concentrated and the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM to provide 1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate. Yield: 1.04 g (94.70%). 1H NMR (DMSO-d5) δ 7.95 (d, J=7 Hz, 2H), 7.64 (t, J=7 Hz, 1H), 7.52 (t, J=8 Hz, 2H), 5.08-5.04 (m, 1H), 2.68-2.62 (m, 1H), 2.55-2.40 (m, 4H), 1.70-1.53 (m, 5H), 1.26 (d, J=6 Hz, 3H), 1.19-1.07 (m, 5H), 0.93 (t, J=7 Hz, 3H). LCMS: m/z=290.4 [M+H], RT=3.93 min, (Column: Y, Program: P1)

Workup

temperaturethe reaction mixture heated at 60° C. for another 24 hours
filtrationThe reaction mixture was filtered
washwashed 5% methanol-DCM
concentrationThe filtrate was concentrated
customthe crude material was purified by Combiflash® chromatography
washeluting with 6-7% methanol/DCM

Sources & evidence

ORD record: ord-baa4c64e630f494580f414467eb26f15
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09180115B2

Reaction notes

Loading…