6-Chloro-1-hexanol → HCID 54505811, compound

HRID 373979Notes

Reaction equation

HRID 373979 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[OH:9][C@H:10]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:11][NH:12][C@H:13]([CH3:22])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>CS(C)=O>[OH:9][C@H:10]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:11][NH:12][C@H:13]([CH3:22])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 748286-Chloro-1-hexanolHCID 54283524HCID 54283524, compound

Product 1

HCID 54505811HCID 54505811, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

300 ml of 6-chlorohexanol were added to a solution of 602 mg of p-[(R)-2-[[(S)-2-hydroxy-3-phenoxypropyl]-amino]propyl]phenol and 246 mg of potassium t-butylate in 10 ml of dimethylsulfoxide and the reaction mixture was stirred at 80° for 1 hour. The reaction mixture was evaporated in a high vacuum and the residue was chromatographed on silica gel with chloroform/n-propanol/saturated ammonia (1000:50:3), whereby there were obtained 500 mg of pure, amorphous 6-[p-[(R)-2-[[(S)-2-hydroxy-3-phenoxypropyl]amino]propyl]phenoxy]hexanol, [α]D20 =-21° (c=0.9 in methanol), ε222 =17230.

Workup

  1. customThe reaction mixture was evaporated in a high vacuum
  2. customthe residue was chromatographed on silica gel with chloroform/n-propanol/saturated ammonia (1000:50:3)

Sources & evidence

ORD record
ord-129a5c1744694be69260019c64fa6e5d
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

Loading…