Benzene, (1-ethylpropyl)- (8CI)(9CI) → HCID 70197121, compound

HRID 1276507Notes

Reaction equation

HRID 1276507 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]([NH2:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]1([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]([N:20]2[CH2:29][CH2:28][CH:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:30][CH2:31]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14527Benzene, (1-ethylpropyl)- (8CI)(9CI)HCID 81531DiisopropylethylamineHCID 16228925tert-Butyl 3-amino-4-phenylpiperidine-1-carboxylate

Product 1

HCID 70197121HCID 70197121, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

To a solution of amine (from Example 104, Step E) and (±) -1, 5-dibromo, 3-phenyl-pentane in 0.5 mL of isobutylnitrile was added 0.080 mL of DIEA and a catalytic amount of tetrabutyl-ammonium iodide. After warming the reaction to 95° C. for 22 h, the mixture was partitioned between 10 mL of CH2Cl2 and 10 mL 1N NaOH. After separating layers, the aqueous phase was extracted with 10 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography eluting with 10% EtOAc in hexanes to provide 10 mg of the title compound: 1H NMR (300 MHz, CDCl3): δ1.2-1.9 (m, 16H), 2.1-2.4 (m, 2H), 2.6-3.0 (m, 6H), 4.0-4.4 (m, 2H), 7.0-7.4 (m, 10H). RF : 0.45 (20% EtOAc in hexanes).

Workup

  1. temperatureAfter warming
  2. customthe reaction to 95° C. for 22 h
  3. customthe mixture was partitioned between 10 mL of CH2Cl2 and 10 mL 1N NaOH
  4. customAfter separating layers
  5. extractionthe aqueous phase was extracted with 10 mL of CH2Cl2
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography
  9. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-59274f271fcf4dde9603ab35e27ba74b
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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