Hydrochloric Acid → HCID 68541938, compound

HRID 1446693Notes

Reaction equation

HRID 1446693 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16](I)[CH:17]=1)[CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(=[NH:32])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].Cl.[OH-].[Na+].[Cl-].[Na+]>C(OCC)(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.O.C1COCC1>[C:1]([C:5]1[CH:17]=[C:16]([NH2:32])[CH:15]=[C:7]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 68546115HCID 68546115, compound

Product 1

HCID 68541938HCID 68541938, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Combine 4-(3-tert-butyl-5-iodo-benzyl)-morpholine (0.785 g, 2.2 mmol), benzophenone imine (0.44 mL, 1.2 equiv.), sodium tert-butoxide (0.29 g, 1.4 equiv.), racemic BINAP (0.061 g, 4.5 mol %), and THF (10 mL). De-gas with nitrogen then add bis(dibenzylideneacetone) palladium (0.037 g, 3 mol %) and heat reaction at 50° C. overnight under nitrogen. In the morning add approximately 4 mL of 5 N HCl (aq) and heat for one hour at 50° C. Let cool to room temperature then dilute with ethyl acetate and make basic with 1 N NaOH (aq). Wash organics with water then aqueous saturated sodium chloride. Dry organics with MgSO4, filter and concentrate in vacuo. Purify on silica gel (4:1 Hexanes:Ethyl Acetate→10% Methanol: DCM) to give product (0.449 g, 83%). MS (ES), m/z 249.3 (M+1).

Workup

  1. customDe-gas with nitrogen
  2. temperatureadd bis(dibenzylideneacetone) palladium (0.037 g, 3 mol %) and heat
  3. customreaction at 50° C. overnight under nitrogen
  4. temperatureLet cool to room temperature
  5. filtrationDry organics with MgSO4, filter
  6. concentrationconcentrate in vacuo
  7. customPurify on silica gel (4:1 Hexanes:Ethyl Acetate→10% Methanol: DCM)

Sources & evidence

ORD record
ord-2a0bb051329c47f8bb0a94c56759f3d6
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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