Water → HCID 14391214, compound

HRID 1681351Notes

Reaction equation

HRID 1681351 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[CH2:16]([O:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].O>CC(C)=O>[CH2:16]([O:22][CH2:23][CH2:24][CH2:25][NH:26][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:9])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 855803-(Hexyloxy)propylamineHCID 185583(R,R)-Stilbene oxide

Product 1

HCID 14391214HCID 14391214, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of trans-stilbene oxide (1.96 g, 0.010 mol) and 3-hexyloxypropylamine (1.75 g, 0.011 mol) was heated at 140° C. for 6 hours. After standing at ambient temperature for 44 hours, the reaction mixture was dissolved in acetone (10 mL) and the solution poured into water (150 mL). The light brown oil that separated from solution solidified on standing for 1 hour. The solid was collected and dried on absorbent paper for 18 hours. The solid was then triturated in isooctane (soluble) and the solution chilled to obtain a solid that was collected, washed with cold isooctane, and dried under ambient conditions to obtain 1.20 g (34%) of the product; mp 67°-69° C.

Workup

  1. customThe light brown oil that separated from solution
  2. waiton standing for 1 hour
  3. customThe solid was collected
  4. customdried on absorbent paper for 18 hours
  5. customThe solid was then triturated in isooctane (soluble)
  6. temperaturethe solution chilled
  7. customto obtain a solid
  8. customthat was collected
  9. washwashed with cold isooctane
  10. customdried under ambient conditions

Sources & evidence

ORD record
ord-87b164941fdf474d836737ec7e53bc8b
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

Loading…