N,N,N',N'-Tetramethylethylenediamine → HCID 23121954, compound

HRID 1713486Notes

Reaction equation

HRID 1713486 reaction equation
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8]2[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=[O:15])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)CCN(C)C.C([Li])(CC)C.C1CCCCC1.[CH:52]1([C:58]([CH:60]2[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]2)=[O:59])[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH:60]1([C:58]2([CH:52]3[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]3)[CH:10]3[CH2:9][N:8]([C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:13][CH2:12][N:11]3[C:14](=[O:15])[O:59]2)[CH2:61][CH2:62][CH2:63][CH2:64][CH2:65]1

Participants

9

Reactant 6

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 8403Methanone, dicyclohexyl-HCID 25517Ammonium ChlorideHCID 23122085HCID 23122085, compoundHCID 178418400CID 53628100

Product 1

HCID 23121954HCID 23121954, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

1,1-Dimethylethyl 4-(triphenylmethyl)-1-piperazine carboxylate (1.0 g, 2.3 mmol) and tetramethylethylenediamine (1.0 g, 8.6 mmol) were dissolved in tetrahydrofuran (10 mL), which was cooled to −78° C. A 1.0 M solution of sec-butyllithium in hexane and cyclohexane (7.2 mL, 7.2 mmol) was added thereto, and the mixture was stirred for 2 hours and the temperature was elevated to −50° C. After cooling to −78° C. again, a solution of dicyclohexyl ketone (1.1 g, 5.9 mmol) in tetrahydrofuran (10 mL) was added dropwise thereto, and the mixture was stirred for 15 hours while elevating the temperature to room temperature. To the reaction solution was added an aqueous saturated ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:3) to obtain the title compound (0.95 g, yield 74%).

Workup

  1. customwas elevated to −50° C
  2. temperatureAfter cooling to −78° C. again
  3. stirringthe mixture was stirred for 15 hours
  4. customto room temperature
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-f71f2326a4a3406492fcfd8298931ed2
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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