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Iodoethane → HCID 86681545, compound

HRID 709015
Notes
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Reaction equation

HRID 709015 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 10770HexylcaineHCID 11430Potassium Carbonate

Product 1

HCID 86681545HCID 86681545, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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

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

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