Ammonia → HCID 18705587, compound

HRID 2287808Notes

Reaction equation

HRID 2287808 reaction equation
Cl.C([O:4][C:5](=O)[CH:6]([NH2:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])C.[NH3:27]>CO>[NH2:25][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]([NH2:27])=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18705582HCID 18705582, compound

Product 1

HCID 18705587HCID 18705587, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A slurry of ethyl-2-aminoeicosanoate hydrochloride prepared as in Example 28B (74.2 g, 0.189 mol) in anhydrous methanol (500 ml) was saturated with anhydrous ammonia at 0° C. The resulting mixture was sealed in a pressure bottle and heated to 60° C., resulting in a pressure of 40 psi. After 65 h at 60° C., the crystalline mixture was cooled to -20° C. and the solid was filtered to give 57.6 g (93%) of the product as off-white plates: mp 103-4° C.; 1H NMR (CDCl3) δ 0.88 (t, J=6.5 Hz, 3 H), 1.37 (m, 35 H), 1.82 (m, 1 H), 3.67 (m, 1 H), 5.30 (br s, 1 H), 7.09 (br s, 1 H).

Workup

  1. customThe resulting mixture was sealed in a pressure bottle
  2. customresulting in a pressure of 40 psi
  3. temperaturethe crystalline mixture was cooled to -20° C.
  4. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-084e2e1ccf904b4f86646bab9f019993
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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