Hydrochloric Acid → HCID 86692452, compound

HRID 1748501Notes

Reaction equation

HRID 1748501 reaction equation
C(=[NH:14])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].Br[C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH2:33][CH2:32][CH:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH2:30][CH:29]=2)=[N:26][CH:27]=1.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[N:34]1([CH:31]2[CH2:32][CH2:33][C:28]([C:25]3[N:26]=[CH:27][C:22]([NH2:14])=[CH:23][CH:24]=3)=[CH:29][CH2:30]2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 86692453HCID 86692453, compound

Product 1

HCID 86692452HCID 86692452, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Palladium (II) acetate (65 mg), benzophenonimine (4.1 ml), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (180 mg) and sodium tert-butoxide (3.33 g) were added to a toluene solution (51 ml) of 4-[4-(5-bromopyridin-2-yl)cyclohex-3-en-1-yl]morpholine (7.46 g) described in Reference Example 77, and stirred at 120° C. for two hours. After completion of the reaction, the reaction vessel was taken out from an oil bath, 3N hydrochloric acid aqueous solution (50 ml) was added and the mixture was stirred at room temperature for two hours. Next, the reaction solution was filtered through Celite, the aqueous layer of the filtrate was separated from the organic layer with a separating funnel. The resulting aqueous layer was cooled to 0° C., 1N aqueous solution of sodium hydroxide was added and the precipitated solid was filtered. The resulting residue was purified with NH silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (5.73 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction vessel was taken out from an oil bath
  3. stirringthe mixture was stirred at room temperature for two hours
  4. filtrationNext, the reaction solution was filtered through Celite
  5. customthe aqueous layer of the filtrate was separated from the organic layer with a separating funnel
  6. temperatureThe resulting aqueous layer was cooled to 0° C.
  7. addition1N aqueous solution of sodium hydroxide was added
  8. filtrationthe precipitated solid was filtered
  9. customThe resulting residue was purified with NH silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a939b3a2c3a74cb5a94c1af0c85650e2
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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