Benzene, (3-bromopropoxy)- → HCID 23036366, compound

HRID 1709913Notes

Reaction equation

HRID 1709913 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:9]#[N:10])=[CH:4][CH:3]=1.[O:23]([CH2:30][CH2:31][CH2:32]Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:34](=[O:37])([OH:36])[O-].[K+].CO.C([O:43]CC)C>C1C=CC=CC=1.C(Cl)(Cl)Cl>[C:30]([OH:23])(=[O:43])[C:34]([OH:36])=[O:37].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:32][CH2:31][CH2:30][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 68522Benzene, (3-bromopropoxy)-HCID 516893Potassium BicarbonateHCID 14407188HCID 14407188, compoundHCID 21864698Diethyl ether methanol

Product 1

HCID 23036366HCID 23036366, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

A mixture of α-(4-fluorophenyl)-α-(4-piperidinyl)2-pyridineacetonitrile (11.30 g, 0.0383 mole), 3-phenoxypropyl bromide (8.20 g, 0.0383 mole), and potassium bicarbonate (4.0 g, 0.04 mole) was heated overnight at reflux in 350 ml of acetonitrile (dried over 4A molecular sieves). The reaction mixture was cooled to room temperature and filtered, and solvent removed by rotary evaporation. A dark brown oil was obtained and dissolved in chloroform. The chloroform layer was extracted with 5% sodium hydroxide and water, dried over sodium sulfate and filtered, and the solvent was removed to give a brown oil. A 0.55 g sample of the oil was converted to the oxalate salt in methanol-ethyl ether. A white, crystalline solid was isolated and dried in vacuo overnight at 80° C., to give 0.35 g (48.4% yield) of product, mp 121°-125° C.

Workup

  1. temperaturewas heated overnight
  2. filtrationfiltered
  3. customsolvent removed by rotary evaporation
  4. customA dark brown oil was obtained
  5. extractionThe chloroform layer was extracted with 5% sodium hydroxide and water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed
  9. customto give a brown oil
  10. customA white, crystalline solid was isolated
  11. customdried in vacuo overnight at 80° C.

Sources & evidence

ORD record
ord-034ed532421941a6bbdcdfbc4cb41522
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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