Dimethylamine → HCID 14924451, compound

HRID 483295Notes

Reaction equation

HRID 483295 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH3:13][NH:14][CH3:15]>CS(C)=O>[CH:10]1([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:14]([CH3:15])[CH3:13])=[CH:3][CH:4]=2)=[O:9])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 69876Cyclopropyl 4-fluorophenyl ketone

Product 1

HCID 14924451HCID 14924451, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopropyl p-fluorophenyl ketone (1.12 g, 6.9 mmol) is added to 3 ml of dimethylsulfoxide (DMSO). The flask is sealed with a septum and the solution stirred and cooled to 0° C. in an ice bath. Anhydrous dimethylamine (3.4 g, 75.5 mmol) is added by syringe and the solution is gradually warmed to room temperature and allowed to stir at room temperature for 72 hrs. The precipitate is filtered and washed with DMSO and ether. Recrystallization from acetone-pentane (1:1) yielded p-N,N-dimethylaminophenyl cyclopropyl ketone as a white crystalline solid (1.22 g, 92.8%); m.p. 139°-141° C.; IR (KBr):158 cm-1 (C=O); NMR (CDCl3) δ:0.99 (m,2H); 1.16 (m,2H ) 2.60 (m,1H); 3.05 (s,6H); 6.67 (d,2H); 7.96 (d,2H).

Workup

  1. customThe flask is sealed with a septum
  2. temperaturethe solution is gradually warmed to room temperature
  3. stirringto stir at room temperature for 72 hrs
  4. filtrationThe precipitate is filtered
  5. washwashed with DMSO and ether
  6. customRecrystallization from acetone-pentane (1:1)

Sources & evidence

ORD record
ord-3d2cc5133a4d40fda5095b78e60739ed
Source dataset
uspto-grants-1993_07
Patent number
USH0001209

Reaction notes

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