Diethyl Ether → Ethyl 4-aminocyclohexanecarboxylate

HRID 2298969Notes

Reaction equation

HRID 2298969 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.O=S(Cl)Cl.[CH3:15][CH2:16]OCC>CCO>[CH2:15]([O:9][C:8]([CH:5]1[CH2:6][CH2:7][CH:2]([NH2:1])[CH2:3][CH2:4]1)=[O:10])[CH3:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 1715604-Aminocyclohexanecarboxylic acid

Product 1

HCID 409963Ethyl 4-aminocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-amino-cyclohexanecarboxylic acid (G) (5 g, 35 mmol) in EtOH (175 mL) at 0° C. was added SOCl2 (12.6 mL, 174 mmol) dropwise via a syringe. The reaction mixture was warmed to room temperature and stirred for 16 h. After concentration of the reaction mixture, ether was added and the suspension was filtered to give 4-amino-cyclohexanecarboxylic acid ethyl ester (H) (mixture of cis/trans) as a white solid (4.8 g): 1H NMR (300 MHz, CDCl3) δ8.35 (br s, 3 H), 4.18 (m, 2 H), 3.36-3.15 (m, 1 H), 2.54 (m, 1 H), 2.30-1.45 (series of m, 8 H), 1.13 (t, 3 H); mass spectrum m/z 172 [(M+H)+; calcd for C9H18NO2: 172].

Workup

  1. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-7a5b6d02e04b43f4a4f3d13679907d8e
Source dataset
uspto-grants-2002_12
Patent number
US06495561B2

Reaction notes

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