Diethyl Ether → HCID 87678330, compound

HRID 2421447Notes

Reaction equation

HRID 2421447 reaction equation
C[Mg+].[Br-].CCOCC.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C:15]([C:17]1[C:18]2[C:23]([CH:24]=[C:25]3[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]3)=[CH:22][CH:21]=[CH:20][CH:19]=2)#[N:16]>C1(C)C=CC=CC=1>[CH:29]1[C:30]2[C:25](=[CH:24][C:23]3[C:18]([C:17]=2[C:15](=[NH:16])[N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 145869-CyanoanthraceneHCID 178418689HCID 178418689, compound

Product 1

HCID 87678330HCID 87678330, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of MeMgBr in ether (3.3 mL, 3.0 M, 9.9 mmol) was added to a solution of piperidine (1.11 g, 13.1 mmol) in toluene (50 mL) at 50° C. The mixture was stirred for 1 h and a white precipitate formed. Next, the mixture was cooled to 0° C. and 9-cyanoantracene (2.00 g, 9.9 mmol) was added. The mixture was allowed to warm to room temperature and the mixture was stirred for 16 h subsequently. The conversion, determined by GC, appeared to be 98%. The mixture was quenched with an aqueous NH4Cl solution (1%, 150 mL). The organic phase was separated from the aqueous phase and the latter was extracted with CH2Cl2 (250 mL) twice. The combined organic phases were dried over Na2SO4, filtered and the solvents were removed under reduced pressure resulting in a sticky residue. Pure product 1.76 g (62%) was obtained by rinsing the residue with ligroin. The ligand was characterized by 1H NMR (300 MHz) (CDCl3) δ (ppm): 8.4 (s, 1H), 7.9 (m, 4H), 7.4 (m, 4H), 5.8 (bs, 1H), 4.0 (bt, 2H), 2.7 (bt, 2H), 1.8 (bm, 2H), 1.5 (p, 2H), 1.2 (bm, 2H) and by 13C-NMR (75.5 MHz) (CDCl3) δ (ppm): 163.3, 130.7, 129.4, 126.6, 125.8, 125.3, 124.6, 123.8, 123.5, 46.5, 41.8, 25.0, 23.8, 22.8.

Workup

  1. customa white precipitate formed
  2. temperatureto warm to room temperature
  3. stirringthe mixture was stirred for 16 h subsequently
  4. customThe mixture was quenched with an aqueous NH4Cl solution (1%, 150 mL)
  5. customThe organic phase was separated from the aqueous phase
  6. extractionthe latter was extracted with CH2Cl2 (250 mL) twice
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customresulting in a sticky residue

Sources & evidence

ORD record
ord-77eb7249996b4b92b89878ca6c6c4c59
Source dataset
uspto-grants-2011_06
Patent number
US07956140B2

Reaction notes

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