Malonic Acid → 2-(1-Aminocyclohexyl)acetic acid hydrochloride

HRID 1704629Notes

Reaction equation

HRID 1704629 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([OH:14])(=[O:13])[CH2:9]C(O)=O.C([O-])(=O)C.[NH4+:19]>C(O)C>[NH2:19][C:1]1([CH2:9][C:8]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 7967CyclohexanoneHCID 517165Ammonium Acetate

Product 1

HCID 44266932-(1-Aminocyclohexyl)acetic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclohexanone (49 g), malonic acid (52 g), and ammonium acetate (77 g) were heated at reflux for six hours in 95% ethanol (150 ml.). The solution was allowed to cool, the crude product (47 g) collected by filtration and recrystallised from 95% ethanol to yield (1-aminocyclohexyl) acetic acid [(40 g) m.p. 240° C.: (found C, 61.0; H, 9.7; N, 8.9; C8H15NO2 requires C, 61:1; H, 9.6; N, 8.9%) n.m.r. δppm (D2O) 1.5-1.8 (b.s., 10H), 2.5 (s, 2H), i.r.νmax (mull) 2150 cm-1 (s, -NH3(+) overtone), 1610 and 1495 cm-1 (s,s, - NH3(+), 1560 cm-1 (b.s. -CO2(-))].

Workup

  1. temperatureto cool
  2. filtrationthe crude product (47 g) collected by filtration
  3. customrecrystallised from 95% ethanol

Sources & evidence

ORD record
ord-1a0b05d343774858a5c9d5f22852a90e
Source dataset
uspto-grants-1978_11
Patent number
US04127570

Reaction notes

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