Cyclohexylamine → HCID 58078880, compound

HRID 532090Notes

Reaction equation

HRID 532090 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O[CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]#[CH:27])(=O)=O)=CC=1>C(O)C>[CH2:25]([O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:26]#[CH:27]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 25199393HCID 25199393, compound

Product 1

HCID 58078880HCID 58078880, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclohexylamine (150 mg, 1.5 mmol, 1 equiv.) and 2-(2-(prop-2-ynyloxy)ethoxy)ethyl 4-methylbenzenesulfonate (s-8) (100 mg, 0.335 mmol, 0.2 equiv.) were dissolved in 1 mL of ethanol. The reaction was allowed to proceed under microwave irradiation at 80° C. for 10 minutes, after which it was concentrated under reduced pressure and chromatographed (Silica Gel, 25 g RediSep pre-packed column, 10% EtOAc:Hexanes→50% EtOAc:Hexanes, followed by EtOAc flush) to give N-(2-(2-(prop-2-ynyloxy)ethoxy)ethyl)cyclohexanamine (s-10) as a clear oil (28 mg, 37%). IR (thin film) 3253 (w), 2924 (s), 2852 (s), 2113 (w), 1449 (m), 1349 (m), 1263 (w), 1102 (s), 919 (w), 839 (w); 1H NMR (400 MHz, CDCl3) δ 4.19 (d, J=2.4 Hz, 2H), 3.70-3.65 (m, 2H), 3.65-3.60 (m, 2H), 3.59 (t, J=5.4 Hz, 2H), 2.80 (t, J=5.4 Hz, 2H), 2.42 (t, J=2.3 Hz, 1H), 2.40-2.34 (m, 1H), 1.90-1.84 (m, 2H), 1.72-1.69 (m, 2H), 1.64-1.54 (m, 1H), 1.30-1.15 (m, 3H), 1.15-0.99 (m, 2H), 0.92-0.81 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 79.6, 74.6, 70.9, 70.1, 69.0, 58.4, 56.8, 42.3, 33.4, 26.2, 25.1. HRMS (ES+) calc'd for C13H23NO2 (M+H) m/z 226.1762 Found 226.1797.

Workup

  1. customto proceed under microwave irradiation at 80° C. for 10 minutes
  2. concentrationafter which it was concentrated under reduced pressure
  3. customchromatographed
  4. custom(Silica Gel, 25 g RediSep pre-packed column, 10% EtOAc:Hexanes→50% EtOAc:Hexanes, followed by EtOAc flush)

Sources & evidence

ORD record
ord-8715c112d60f4d8489b10bb3b69db69d
Source dataset
uspto-grants-2014_10
Patent number
US08852630B2

Reaction notes

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