Water → HCID 21924532, compound

HRID 915494Notes

Reaction equation

HRID 915494 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([N:15]([CH2:25][CH:26]=[CH2:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:13]=[CH2:14].N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[CH2:25]([N:15]([CH2:12][CH:13]=[CH2:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21924501HCID 21924501, compound

Product 1

HCID 21924532HCID 21924532, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Toluene-sulphonyl chloride (12.5 g, 0.066 mol) was added slowly to a stirred solution of 8-diallylaminooctan-1-ol (10.0 g, 0.044 mol) and pyridine (7.0 g, 0.088 mol) in chloroform (100 cm3) at 0° C. After 24 h, water (100 cm3) was added and the solution washed with dilute hydrochloric acid (20%, 100 cm3), sodium carbonate solution (100 cm3), water (100 cm3), dried (MgSO4) and concentrated to a yellow oil which was purified by column chromatography [silica gel, 4% diethyl ether in hexane eluting to DCM:ethanol 10:1] to yield the desired product (6.7 g, yield 40%).

Workup

  1. washthe solution washed with dilute hydrochloric acid (20%, 100 cm3), sodium carbonate solution (100 cm3), water (100 cm3)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to a yellow oil which
  4. customwas purified by column chromatography [silica gel, 4% diethyl ether in hexane eluting to DCM:ethanol 10:1]

Sources & evidence

ORD record
ord-93cc7fe3d7fa45bdb5e2f5bebf8064e4
Source dataset
uspto-grants-2007_09
Patent number
US07265163B2

Reaction notes

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