Octylamine → HCID 54513161, compound

HRID 2392919Notes

Reaction equation

HRID 2392919 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[CH2:11][CH:12]([OH:23])[CH2:13][N:14]([CH2:20][CH2:21][OH:22])[CH2:15][CH:16]([OH:19])[CH2:17]Cl>C1(C)C(C)=CC=CC=1>[OH:23][CH:12]([CH2:13][N:14]([CH2:20][CH2:21][OH:22])[CH2:15][CH:16]([OH:19])[CH2:17][NH:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:11][NH:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 8143OctylamineHCID 57319167HCID 57319167, compound

Product 1

HCID 54513161HCID 54513161, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
70 °C

Procedure

A reactor was charged with 275 g (2.2 moles) of octylamine, and the contents were heated to 70° C. To the contents, a solution with 36 g (0.17 mole) of N,N-bis(3-chloro-2-hydroxypropyl)hydroxyethylamine dissolved in 30 g of xylene was then added dropwise over 40 minutes. The resultant mixture was aged further for 4 hours. Thereafter, xylene was distilled off under reduced pressure, and unreacted octylamine was then distilled off at 70° C. and 0.5 mmHg. A mixture of 500 ml of xylene and 500 ml of 5% aqueous sodium hydroxide was added to the residue to subject it to extraction and washing. Thereafter, a xylene layer was taken out and concentrated, thereby obtaining 50.7 g (yield: 69%) of 11,15-dihydroxy-13-hydroxyethyl-9,13,17-triazapentacosane represented by the following formula. ##STR13##

Workup

  1. additionwas then added dropwise over 40 minutes
  2. distillationThereafter, xylene was distilled off under reduced pressure, and unreacted octylamine
  3. distillationwas then distilled off at 70° C.
  4. additionA mixture of 500 ml of xylene and 500 ml of 5% aqueous sodium hydroxide
  5. additionwas added to the residue
  6. extractionto extraction
  7. washwashing
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9d887df76e7a46ab95c4b2b5b1814d08
Source dataset
uspto-grants-1998_09
Patent number
US05801270

Reaction notes

Loading…