(+)-Styrene oxide → HCID 18607072, compound

HRID 1906654Notes

Reaction equation

HRID 1906654 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH2:15]1[O:23][C@@H:16]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[OH:23][C@H:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 114705(+)-Styrene oxideHCID 144712494-(3-Aminopropyl)benzene-1-sulfonamide

Product 1

HCID 18607072HCID 18607072, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 20.0 g of 3-(4-aminosulphonylphenyl)-propylamine, 16.8 g (R)-styrene oxide and 500 ml of acetonitrile was heated under reflux for 40 hours. The solvent was then evaporated in vacuo and the residue was chromatographed on 1 kg of silica gel, using with chloroform/n-propanol/25% ammonia (1600:100:4). There was isolated 8.3 g of pure p-[3-[[(R)-β-hydroxyphenethyl]amino]propyl]-benzenesulphonamide of melting point 165°-166° (from acetonitrile). [α]D20 =-13.4° (c=1.0% in methanol); UV: ε224 =14710.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hours
  3. customThe solvent was then evaporated in vacuo
  4. customthe residue was chromatographed on 1 kg of silica gel

Sources & evidence

ORD record
ord-0866519cdfa54f3f95b49ace9a34c9f5
Source dataset
uspto-grants-1987_03
Patent number
US04652679

Reaction notes

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