Diethyl Ether → HCID 178507584, compound

HRID 1748502Notes

Reaction equation

HRID 1748502 reaction equation
[F-].[K+].[N:3]1([CH:9]2[CH2:14][CH2:13][C:12]([C:15]3[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)=[CH:11][CH2:10]2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C(OCC)C>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:3]1([C@@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]3[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[N:3]1([C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]3[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 86692452HCID 86692452, compound

Product 2

HCID 178507584HCID 178507584, compoundHCID 178507585HCID 178507585, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium (II) acetate (519 mg) and an aqueous solution (23 ml) of potassium fluoride (2.69 g) was added at room temperature to a solution of 6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridin-3-amine (3.0 g) described in Reference Example 78 in tetrahydrofuran (115 ml), poly(methylhydrosiloxane) (2.8 ml) was added dropwise and the mixture was stirred at the same temperature for an hour. After completion of the reaction, diethyl ether (115 ml) was added, the reaction solution was filtered through Celite and the filtrate was concentrated. Saturated brine was added to the resulting solution and extracted with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with NH silica gel column chromatography (n-hexane/ethyl acetate) to give cis-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (1.45 g) and trans-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (906 mg) as a white solid respectively.

Workup

  1. additionwas added
  2. filtrationthe reaction solution was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. additionSaturated brine was added to the resulting solution
  5. extractionextracted with ethyl acetate three times
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue was purified with NH silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0ca8772bdf334112827eef793410c8c7
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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