Acetic Acid → 4-(Benzylamino)-1-methylcyclohexanol

HRID 1500886Notes

Reaction equation

HRID 1500886 reaction equation
[OH:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl>[CH2:10]([NH:17][CH:5]1[CH2:6][CH2:7][C:2]([CH3:9])([OH:1])[CH2:3][CH2:4]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 285394-Hydroxy-4-methylcyclohexanoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 674652054-(Benzylamino)-1-methylcyclohexanolYield 81.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4-hydroxy-4-methylcyclohexanone (4.1 g, 32.0 mmol) and benzyl amine (6.8 g, 64.0 mmol) in 1,2-dichloroethane (120 mL) was added acetic acid (3.84 g, 64.0 mmol). After the resulting mixture was stirred at RT for 2 hours, the mixture was added NaBH(OAc)3 (13.6 g, 64.0 mmol). The resulting mixture was then stirred at RT overnight. After the reaction was completed, the mixture was basified to pH 11 by addition of 2 N NaOH. The separated organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel (MeOH:DCM=3:100 to 1:10) to afford 4-(benzylamino)-1-methylcyclohexanol as a white solid (5.7 g, yield: 80.0%).

Workup

  1. stirringThe resulting mixture was then stirred at RT overnight
  2. concentrationThe separated organic layer was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (MeOH:DCM=3:100 to 1:10)

Sources & evidence

ORD record
ord-85631cfc45d64bad8f263c7123fb1cbe
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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