4-(Aminomethyl)cyclohexanecarboxylic acid → Cyclohexanemethanol, 4-(aminomethyl)-

HRID 919108Notes

Reaction equation

HRID 919108 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9](O)=[O:10])[CH2:5][CH2:4]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 55264-(Aminomethyl)cyclohexanecarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 70631Cyclohexanemethanol, 4-(aminomethyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Aminomethyl)cyclohexanecarboxylic acid (4.00 g, 25.44 mmol) was stirred in THF (100 mL) at 0° C. under a nitrogen atmosphere. LiAlH4 (2.90 g, 76.33 mmol) was then added and the reaction allowed to warm to RT and stir for 3 h. It was then cooled to 0° C. and quenched with H2O. Na2SO4 was then added and the mixture stirred for 10 minutes. It was then filtered through celite and the filtrate concentrated in vacuo to give the product as a colourless oil which solidified on standing to give the product as a white solid (3.72 g, 100%). 1H NMR (300 MHz, d6-DMSO) δ: 0.95 (4H, m), 1.22-1.47 (5H, m), 1.86 (4H, m), 2.55 (2H, d, J=6.6 Hz), 4.46 (2H, d, J=6.3 Hz).

Workup

  1. temperatureIt was then cooled to 0° C.
  2. customquenched with H2O
  3. additionNa2SO4 was then added
  4. stirringthe mixture stirred for 10 minutes
  5. filtrationIt was then filtered through celite
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2aecfd0dc00c435984aaa418f2339862
Source dataset
uspto-grants-2016_03
Patent number
US09273003B2

Reaction notes

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