Cyclohexanone → N-(2-methoxyethyl)cyclohexanamine

HRID 1746666

Reaction equation

HRID 1746666 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][O:9][CH2:10][CH2:11][NH2:12].[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH3:8][O:9][CH2:10][CH2:11][NH:12][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 80182-MethoxyethylamineHCID 4311764Sodium borohydride

Product 1

HCID 12687399N-(2-methoxyethyl)cyclohexanamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of cyclohexanone (10 g, 0.10 mol) in Toluene (100 ml) was treated with 2-methoxy ethylamine (8.4 g, 0.11 mol) and refluxed at 110° C. for 3 h. The reaction mass was cooled and diluted with ethanol (50 ml) and sodium borohydride (5.8 g, 0.15 mol) was added in portions at 0° C. The reaction mass was stirred at RT for 12 h and concentrated under reduced pressure. The residue was dissolved in water (100 ml), extracted with DCM (2×100ml), dried over sodium sulphate and evaporated. The crude material was purified by column chromatography by using DCM and methanol (98:2) as eluent to afford the title compound as a pale yellow liquid.

Workup

  1. temperatureThe reaction mass was cooled
  2. additionwas added in portions at 0° C
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (100 ml)
  5. extractionextracted with DCM (2×100ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-e2fec3e371b4493488aca5402d601f51
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Linked notes

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