Ethanol → Ethyl 4-aminocyclohexanecarboxylate

HRID 1399977Notes

Reaction equation

HRID 1399977 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:15][CH2:16]O>>[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:15][CH3:16])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1715604-Aminocyclohexanecarboxylic acid

Product 1

HCID 409963Ethyl 4-aminocyclohexanecarboxylate

Conditions

Temperature
80 °C

Procedure

To an ice-cold solution of 4-aminocyclohexanecarboxylic acid (5.0 g, 34.92 mmol) in EtOH (20 mL) was added thionyl chloride (7.60 mL, 104.76 mmol). The mixture was heated at 80° C. for 3 h. The solvent was evaporated in vacuo to obtain i (7.23 g). 1H NMR (400 MHz, DMSO-d6): δ 4.19 (q, J=7.20 Hz, 2H), 3.71 (m, 1H), 2.71 (m, 1H), 2.06 (m, 2H), 1.90 (m, 2H), 1.69 (m, 2H), 1.55 (m, 2H), and 1.25 (t, J=7.20 Hz, 3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto obtain i (7.23 g)

Sources & evidence

ORD record
ord-e679fe3ceca04991b083d0f814d264c6
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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