1-Benzyl-4-piperidylamine → HCID 9842076, compound

HRID 1765448Notes

Reaction equation

HRID 1765448 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([N:17]([CH2:27][CH3:28])[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1)[CH3:16].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.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:22]2[CH:23]=[CH:24][C:19]([C:18]([N:17]([CH2:15][CH3:16])[CH2:27][CH3:28])=[O:26])=[CH:20][CH:21]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 4158521-Benzyl-4-piperidylamineHCID 634876Binap, (A+-)-HCID 44982544-bromo-N,N-diethylbenzamideHCID 23676156Sodium t-butoxide

Product 1

HCID 9842076HCID 9842076, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

To a dry flask containing 1-benzyl-piperidin-4-ylamine 6 (5.0 mL; 1.2 eq) in dry toluene (75 mL) was added N,N-diethyl-4-bromobenzamide (5.24 g; 1.0 eq), BINAP (383 mg; 0.03 eq), palladium acetate (92 mg; 0.02 eq) and sodium tert-butoxide (2.75 g; 1.4 eq). The reaction was heated to 80° C. under nitrogen. After 2 hours the reaction was cooled, diluted with ethyl acetate and washed with two portions water. The organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with 5% to 10% methanol in dichloromethane. The residue obtained was boiled in ethyl acetate, cooled and collected by filtration. A pale yellow solid was obtained (5.724 g; 77% yield).

Workup

  1. temperatureAfter 2 hours the reaction was cooled
  2. washwashed with two portions water
  3. dry with materialThe organics were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5% to 10% methanol in dichloromethane
  8. customThe residue obtained
  9. temperaturecooled
  10. filtrationcollected by filtration
  11. customA pale yellow solid was obtained (5.724 g; 77% yield)

Sources & evidence

ORD record
ord-b7510b1d47304214b9772bd003337c5f
Source dataset
uspto-grants-2007_06
Patent number
US07226933B2

Reaction notes

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