Cyclohexanone → HCID 13756690, compound

HRID 556496Notes

Reaction equation

HRID 556496 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:8]1([CH2:14][CH2:15][NH2:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[BH3-]C#N.[Na+]>CO>[CH:1]1([NH:16][CH2:15][CH2:14][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 4082852-MorpholinoethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13756690HCID 13756690, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclohexanone (2.00 g, 20.4 mmol) and 2-morpholin-4-yl-ethylamine (2.98 mL, 20.4 mmol) were dissolved in 10 mL methanol. The solution was stirred at room temperature for an hour. NaBH3CN (1.62 g, 24.4 mmol) was slowly added portionwise in the solution. After the addition, the mixture was stirred at room temperature for 4 hour then concentrated under reduced pressure. To the residue was added 50 mL water and the mixture was adjusted to PH=10 with dilute aqueous KOH and extracted with ethyl acetate. The organic solution was dried with Na2SO4 and concentrated in vacuo to give an oil. MS: 213(M+H)+.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 4 hour
  3. concentrationthen concentrated under reduced pressure
  4. additionTo the residue was added 50 mL water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic solution was dried with Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give an oil

Sources & evidence

ORD record
ord-8dbaa499f3e44952bc8f242d3da16f25
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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