Acetic Acid → 4-(Cyclopropylamino)cyclohexanol

HRID 509280Notes

Reaction equation

HRID 509280 reaction equation
O[CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH:9]1([NH2:12])[CH2:11][CH2:10]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl>[CH:9]1([NH:12][CH:2]2[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]2)[CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 5437064-HydroxycyclohexanoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 674688554-(Cyclopropylamino)cyclohexanolYield 96.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-hydroxycyclohexanone (443 mg, 3.88 mmol) was dissolved in 1,2-dichloroethane (20 ml), followed by sequential addition of cyclopropylamine (0.295 ml, 4.27 mmol), NaBH(OAc)3 (1.3 g, 6.21 mmol), and acetic acid (0.2 ml, 3.88 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 13 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, and extracted with 10% MeOH/MC (15 ml×4). The organic layer was dried over anhydrous sodium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 580 mg of yellow solid (96%).

Workup

  1. customThe resulting reaction liquid
  2. extractionextracted with 10% MeOH/MC (15 ml×4)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfollowed by filtration, concentration, and vacuum
  5. customdrying

Sources & evidence

ORD record
ord-9665846892b6482b9427b017797db0fe
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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