4-Piperidinone, 2,2,6,6-tetramethyl-, monohydrate → (2,2,6,6-Tetramethyl-4-hydroxy-4-piperidinyl)bis(2-cyanoethyl)phosphine oxide

HRID 918234Notes

Reaction equation

HRID 918234 reaction equation
O.[CH3:2][C:3]1([CH3:12])[CH2:8][C:7](=[O:9])[CH2:6][C:5]([CH3:11])([CH3:10])[NH:4]1.[C:13]([CH2:15][CH2:16][PH:17](=[O:22])[CH2:18][CH2:19][C:20]#[N:21])#[N:14]>C(N(CC)CC)C.C(O)(C)C>[CH3:2][C:3]1([CH3:12])[CH2:8][C:7]([P:17](=[O:22])([CH2:18][CH2:19][C:20]#[N:21])[CH2:16][CH2:15][C:13]#[N:14])([OH:9])[CH2:6][C:5]([CH3:11])([CH3:10])[NH:4]1

Participants

5

Reactant 2

HCID 223976024-Piperidinone, 2,2,6,6-tetramethyl-, monohydrateHCID 178511210HCID 178511210, compound

Product 1

HCID 21521477(2,2,6,6-Tetramethyl-4-hydroxy-4-piperidinyl)bis(2-cyanoethyl)phosphine oxideYield 65%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 3776IsopropanolSolvent

Procedure

To 100 milliliters of isopropanol was added 8.65 grams (0.05 mole) of 2,2,6,6-tetramethyl-4-piperidone hydrate; 7.81 grams (0.05 mole) of bis(2-cyanoethyl)phosphine oxide; and 1 gram of triethylamine as catalyst. The reaction mixture was refluxed four hours, cooled in an ice bath, and the crystalline product filtered off. After recrystallization, there was obtained 10.0 grams of white crystalline product of 128°-130°C. melting point, representing a 65% yield.

Workup

  1. temperatureThe reaction mixture was refluxed four hours
  2. temperaturecooled in an ice bath
  3. filtrationthe crystalline product filtered off
  4. customAfter recrystallization

Sources & evidence

ORD record
ord-a7a8c00de87c44faa87768b4ab2ec999
Source dataset
uspto-grants-1976_07
Patent number
US03970636

Reaction notes

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