Benzhydrol → HCID 19850789, compound

HRID 1607700Notes

Reaction equation

HRID 1607700 reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][N:36]([CH2:39][CH2:40]Cl)[CH2:35][CH2:34]2)=[CH:24][CH:23]=1>C(O)(C)(C)C>[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][O:14][CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:35][CH2:34]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 19850790HCID 19850790, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19850789HCID 19850789, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

10.1 g of benzhydrol are refluxed with 6.2 g of potassium tertiary butoxide in 100 ml of anhydrous tertiary butanol under argon gas for 30 minutes, then 19.6 g of 1-[3-[(4-fluorophenyl)-phenylmethoxy]propyl]-4-(2-chloroethyl)piperazine dissolved in 40 ml of anhydrous tertiary butanol are dropwise added. The mixture is boiled for one additional hour, then evaporated to about 40 ml under reduced pressure and after adding water it is extracted with benzene. The organic phase is dried over anhydrous magnesium sulfate and, after evaporating benzene under reduced pressure, the residue is fractionally distilled. The aimed compound boils at 247°-250° C./0.01 Hgmm.

Workup

  1. additionare dropwise added
  2. customevaporated to about 40 ml under reduced pressure
  3. additionafter adding water it
  4. extractionis extracted with benzene
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  6. customafter evaporating benzene under reduced pressure
  7. distillationthe residue is fractionally distilled

Sources & evidence

ORD record
ord-b51c3398b23e4eb7b67e014885afa270
Source dataset
uspto-grants-1989_09
Patent number
US04866062

Reaction notes

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