Acetic Acid → 4-methyl-N-(3-methylbutyl)cyclohexan-1-amine

HRID 1881061Notes

Reaction equation

HRID 1881061 reaction equation
[OH-].[Na+].[CH:3](=O)[CH2:4][CH:5]([CH3:7])[CH3:6].[CH3:9][C:10](O)=O.[C:13]([BH3-])#[N:14].[Na+].[CH2:17]1[CH2:21]O[CH2:19][CH2:18]1.CO>O>[CH3:6][CH:5]([CH3:7])[CH2:4][CH2:3][NH:14][CH:13]1[CH2:10][CH2:9][CH:17]([CH3:21])[CH2:18][CH2:19]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 115523-MethylbutanalHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 213556364-methyl-N-(3-methylbutyl)cyclohexan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-trans-methyl-cyclohexylamine hydrochloride (15 g, 100 mmol) in THF-MeOH (2:1, 200 mL) was added solid NaOH (6.01 g, 150 mmol). The mixture was stirred for 30 m before isovaleraldehyde (10.4 g, 120 mmol), 20 mL AcOH was added. Subsequently sodium cyanoborohydride (6.0 g, 150 mmol) was added in small portions. The reaction mixture was stirred for 18 h before H2O (200 mL) was added and the mixture was extracted with DCM (2×100 mL). The organic fraction were dried (MgSO4) before an excess of HCl in diethyl ether were added. The solvent were removed in vacuo and diethyl ether was added (200 mL). The precipitate was filtered off washed with diethyl ether and dried in vacuo to give 18.8 g of (3-methyl-butyl) -(4-methyl-cyclohexyl)-amine.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with DCM (2×100 mL)
  4. dry with materialThe organic fraction were dried (MgSO4) before an excess of HCl in diethyl ether
  5. additionwere added
  6. customThe solvent were removed in vacuo and diethyl ether
  7. additionwas added (200 mL)
  8. filtrationThe precipitate was filtered off
  9. washwashed with diethyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-92dabe3b82ea44f9810709e4345bd525
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

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