Triethylamine → HCID 178521573, compound

HRID 706905Notes

Reaction equation

HRID 706905 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14]Br.C(N(CC)CC)C>C(#N)C>[O:12]1[CH2:13][CH2:14][N:1]([C@H:2]2[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21521Bis(2-bromoethyl) etherHCID 178511715HCID 178511715, compound

Product 1

HCID 178521573HCID 178521573, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Trans-4-Aminocyclohexanol (0.5 g), 1-bromo-2-(2-bromoethoxy)ethane (1.07 g) and triethylamine (2.42 mL) were dissolved in anhydrous acetonitrile (20 mL). The reaction mixture was heated at 60° C. overnight. The organic solvent was removed under vacuum. The residue was purified with flash column chromatography on silica gel eluting with 7%-10% methanol in dichloromethane to give the title compound.

Workup

  1. customThe organic solvent was removed under vacuum
  2. customThe residue was purified with flash column chromatography on silica gel eluting with 7%-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-e03f096bf2db457ba59c1a0428f53919
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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