Cyclohexylamine → HCID 10403249, compound

HRID 1744779Notes

Reaction equation

HRID 1744779 reaction equation
[N+:1]([CH2:4][C@:5]1([CH2:12][C:13]([OH:15])=[O:14])[CH2:11][C@@H:10]2[C@H:6]1[CH2:7][CH2:8][CH2:9]2)([O-:3])=[O:2].C1(N)CCCCC1>C(OCC)(=O)C>[CH:4]1([NH2:1])[CH2:5][CH2:11][CH2:10][CH2:6][CH2:7]1.[N+:1]([CH2:4][C@:5]1([CH2:12][C:13]([OH:15])=[O:14])[CH2:11][C@@H:10]2[C@H:6]1[CH2:7][CH2:8][CH2:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 10255676HCID 10255676, compound

Product 1

HCID 10403249HCID 10403249, compoundYield 177.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution of nitro acid of Example 8 (928 g; 4.35 mol) in ethyl acetate (9.6 L) was dried by atmospheric azeotropic distillation at constant volume. After cooling the solution to 40° C., cyclohexylamine (423 g; 4.26 mol) was added over 15 minutes. The resultant slurry was cooled to 20° C. over 4 hours and left to stir for 13 hours at 20° C. The solid was collected by filtration and the damp filter cake washed with ethyl acetate (1.3 L). The isolated solid was then dried in vacuo at 30° C. for 18 hours to give the title compound as a white solid (1.205 Kg) in 91% yield.

Workup

  1. temperatureThe resultant slurry was cooled to 20° C. over 4 hours
  2. waitleft
  3. filtrationThe solid was collected by filtration
  4. washthe damp filter cake washed with ethyl acetate (1.3 L)
  5. customThe isolated solid was then dried in vacuo at 30° C. for 18 hours

Sources & evidence

ORD record
ord-dc9e379f47a846cab451df7e49f63a6a
Source dataset
uspto-grants-2006_03
Patent number
US07018818B2

Reaction notes

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