Water → HCID 53715766, compound

HRID 2255433Notes

Reaction equation

HRID 2255433 reaction equation
OC(O)CN[CH:5]([CH3:7])[CH3:6].[CH2:9]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH3:10].[C:16](Cl)(=[O:19])[CH:17]=[CH2:18].[OH2:21].Cl[CH2:23]Cl>CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C>[CH:9]([N:11]([CH2:14][CH2:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH2:12][CH2:13][C:7](=[O:21])[CH:5]=[CH2:6])([CH3:23])[CH3:10]

Participants

8

Reactant 5

HCID 962WaterHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 19738123HCID 19738123, compound

Product 1

HCID 53715766HCID 53715766, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Dihydroxyethyl-isopropylamine (15.06 g, 102.3 mmol) was combined with triethylamine (45.6 ml, 327.35 mmol) and 4-dimethylaminopyridine (1.26 g, 10.23 mmol) in dichloromethane (210 ml). The mixture was cooled, and a solution of acryloyl chloride (1.26 g, 102.23 mmol) in dichloromethane (75 ml) added thereto dropwise over 30 minutes. The mixture was allowed to warm to room temperature and stirring was continued over 21 hours. Water (125 ml) was added, stirring was continued for a further 10 minutes after which the mixture was extracted with ether (375 ml). The extract was dried over sodium sulfate and concentrated to produce an oil which was flash chromotographed on silica gel using hexane/ethyl acetate (97/3) as the elutent. After 6 liters of the elutent had been used, the polarity of the elutent was increased by changing the mixture to 90/10. There was obtained 16 g (62%) of isopropyl-di(acrylylethyl)amine as a clear oil.

Workup

  1. temperatureThe mixture was cooled
  2. waitwas continued over 21 hours
  3. stirringstirring
  4. waitwas continued for a further 10 minutes
  5. extractionafter which the mixture was extracted with ether (375 ml)
  6. dry with materialThe extract was dried over sodium sulfate
  7. concentrationconcentrated
  8. customto produce an oil which
  9. temperaturethe polarity of the elutent was increased

Sources & evidence

ORD record
ord-3815d95ee901428bad5ea082614fa859
Source dataset
uspto-grants-1993_08
Patent number
US05240939

Reaction notes

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