Acrylamide → HCID 19707317, compound

HRID 1655303Notes

Reaction equation

HRID 1655303 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([N:15]1[CH2:19][CH2:18][CH2:17]C1)[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].C(N)(=[O:23])C=C>O>[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[C:11]3[CH2:17][CH2:18][C:19](=[O:23])[NH:15][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6579AcrylamideHCID 57175840HCID 57175840, compound

Product 1

HCID 19707317HCID 19707317, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
89 °C

Procedure

To 6-t-butyl-2-pyrrolidinyl-3,4-dihydronaphthalene (7.25 g; 28.37 mmol) was added 3.0 equiv. of acrylamide (6.05 g; 85.11 mmol). The reaction mixture was stirred at 89° C. overnight. The temperature was then increased to 130° C. and held there for 20 minutes. Water (100 ml) was cautiously added and the reaction mixture was cooled to room temperature. The resulting solid was triturated with water and collected on a filter to afford a brown solid. The soid was recrystallized twice from dimethyl formamide (DMF)/H2O to afford 4.56 g (63% yield) of the subtitle compound. Melting point 265°-268° C.

Workup

  1. temperatureThe temperature was then increased to 130° C.
  2. waitheld there for 20 minutes
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customThe resulting solid was triturated with water
  5. customcollected on
  6. filtrationa filter
  7. customto afford a brown solid
  8. customThe soid was recrystallized twice from dimethyl formamide (DMF)/H2O

Sources & evidence

ORD record
ord-7958f98475654a72986fb4c3c165fa7e
Source dataset
uspto-grants-1993_10
Patent number
US05250539

Reaction notes

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