2,6-Diphenylpiperidine → 1,4-Bis(2,6-diphenylpiperidin-1-yl)-2-butene

HRID 1590798Notes

Reaction equation

HRID 1590798 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1.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:13]1([CH:9]2[CH2:10][CH2:11][CH2:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]2[CH2:6][CH:1]=[CH:2][CH2:3][N:8]2[CH:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:10][CH2:11][CH2:12][CH:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 130106382,6-Diphenylpiperidine

Product 1

HCID 543523251,4-Bis(2,6-diphenylpiperidin-1-yl)-2-buteneYield 61%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,6-diphenylpiperidine [3.0 g, 12.6 mmol; prepared by the method of V. Baliah et al., Indian J. Chem., 16B, 1965 (1978)] and 1,4-but-2-enediol diacetate (1.1 g, 6.3 mmol) in tetrahydrofuran (20 ml, THF) is treated with tetrakis(triphenylphosphine)palladium (0) (0.65 g, 0.6 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a solid that 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 giving an orange solid which is purified by crystallization from methanol to yield 2.02 g (61%) of the title compound as a white solid melting at 197°-200° C.

Workup

  1. customprepared by the method of V
  2. concentrationThe reaction mixture is concentrated in vacuo to a solid
  3. dissolutionthat is redissolved in THF (100 ml)
  4. additiontreated with 20% aqueous sodium hydroxide (25 ml)
  5. stirringThe mixture is stirred for one hour
  6. concentrationconcentrated
  7. extractionextracted with diethyl ether
  8. dry with materialThe ether extracts are dried
  9. concentrationconcentrated
  10. customgiving an orange solid which
  11. customis purified by crystallization from methanol

Sources & evidence

ORD record
ord-57f9b17eac8e4ab8b6b9ee4b6028c6c3
Source dataset
uspto-grants-1993_04
Patent number
US05204474

Reaction notes

Loading…