2,6-Diphenylpiperidine → 1-(2,6-Diphenylpiperidin-1-yl)-4-dibenzylamino-2-butene

HRID 1590799Notes

Reaction equation

HRID 1590799 reaction equation
C(O[CH2:5][CH:6]=[CH:7][CH2:8][N:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)C.[C:24]1([CH:30]2[CH2:35][CH2:34][CH2:33][CH:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:36]1([CH:32]2[CH2:33][CH2:34][CH2:35][CH:30]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:31]2[CH2:5][CH:6]=[CH:7][CH2:8][N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 2

HCID 130106382,6-DiphenylpiperidineHCID 537897791-Acetoxy-4-dibenzylamino-2-butene

Product 1

HCID 543268241-(2,6-Diphenylpiperidin-1-yl)-4-dibenzylamino-2-butene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-acetoxy-4-dibenzylamino-2-butene (3.0 g, 9.8 mmol) and 2,6-diphenylpiperidine (2.3 g, 9.8 mmol) in THF (25 ml) is treated with tetrakis(triphenylphosphine)palladium (0) (0.5 g, 0.45 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo. The residue is redissolved in THF (100 ml) and treated with 20% aqueous sodium hydroxide (25 ml). The mixture is stirred for one hour, concentrated, and extracted with diethyl ether. The ether extracts are dried and concentrated to give an orange oil which is purified by chromatography (silica gel; 5% ethyl acetate in hexanes) to give the title compound in a yield of 2.8 g (59%) as a clear oil. MS m/z 486 (M+)

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is redissolved in THF (100 ml)
  3. additiontreated with 20% aqueous sodium hydroxide (25 ml)
  4. stirringThe mixture is stirred for one hour
  5. concentrationconcentrated
  6. extractionextracted with diethyl ether
  7. dry with materialThe ether extracts are dried
  8. concentrationconcentrated
  9. customto give an orange oil which
  10. customis purified by chromatography (silica gel; 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9f4b96c173f444de95ae1e65f3c16086
Source dataset
uspto-grants-1993_04
Patent number
US05204474

Reaction notes

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