Styrene → HCID 20492274, compound

HRID 434440Notes

Reaction equation

HRID 434440 reaction equation
[C:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:16][C:15]([CH3:18])([CH3:17])[NH:14][C:13]([CH3:20])([CH3:19])[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([OH:35])CCCCC>>[C:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:16][C:15]([CH3:18])([CH3:17])[N:14]([CH2:21][CH:22]([OH:35])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]([CH3:20])([CH3:19])[CH2:12]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 7501StyreneHCID 81031-HexanolHCID 21976021HCID 21976021, compound

Product 1

HCID 20492274HCID 20492274, compound

Procedure

A mixture of 11.45 parts of 4-phenylcarbamoyloxy-2,2,6,6-tetramethylpiperidine and 60 parts of styrene ⟦ocide⟧ oxide in 60 parts of n-hexanol was heated under reflux conditions for 18 hours. The n-hexanol solvent and unreacted styrene oxide were removed by distillation under reduced pressure to yield a pale yellow crystalline solid. Purification by trituration with hot petroleum ether (b.p. 60°-80° C.) yielded 4-phenylcarbamoyloxy-1-[2'-hydroxy-2-'phenylethyl]-2,2,6,6-tetramethylpiperidine having a melting point of 186°-7° C. with the following elemental analysis by weight:

Workup

  1. temperaturewas heated under reflux conditions for 18 hours
  2. customThe n-hexanol solvent and unreacted styrene oxide were removed by distillation under reduced pressure
  3. customto yield a pale yellow crystalline solid
  4. customPurification by trituration with hot petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-a568c0d8709041bba8f9bd16e2231443
Source dataset
uspto-grants-1983_08
Patent number
USRE031342

Reaction notes

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