Hydrochloric Acid → 8-Benzyl-3,8-diazabicyclo[3.2.1]octane

HRID 1743696Notes

Reaction equation

HRID 1743696 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11](CC=C)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1C(=O)CC(=O)N(C)C1=O.P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][NH:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 69860Dimethylbarbituric acidHCID 222355893-Allyl-8-benzyl-3,8-diazabicyclo[3.2.1]octane

Product 1

HCID 120798988-Benzyl-3,8-diazabicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-benzyl-3-(2-propenyl)-3,8-diazabicyclo[3.2.1]octane (22.2 g, 92.7 mmol), 1,3-dimethylbarbituric acid (21.5 g, 137.0 mmol), Pd2(dba)3 (5 g, 5 mmol) and P(C6H5)3 (5.2 g, 20.0 mmol) in methylene chloride (500 mL) was heated at reflux for 16 h. The reaction was poured into 1 N HCl (250 mL) at 0° C. The aqueous acidic layer was separated and made basic with 6 N NaOH, then extracted with ethyl acetate (2×150 mL).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customThe aqueous acidic layer was separated
  4. extractionextracted with ethyl acetate (2×150 mL)

Sources & evidence

ORD record
ord-6033c950d8224b7e93c47b8d72d7f65b
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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