Allyl bromide → HCID 69802498, compound

HRID 1064384Notes

Reaction equation

HRID 1064384 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C@@H:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[C@H:16]([OH:25])[CH2:15]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:28](Br)[CH:29]=[CH2:30].CCOCC.[ClH:37]>C1COCC1.CCOCC>[ClH:37].[CH2:30]([O:25][C@H:16]1[C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[CH2:19][CH2:20][C@@H:14]([CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:11]2)[CH2:15]1)[CH:29]=[CH2:28]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 10953452Ether hydrochlorideHCID 69799954HCID 69799954, compound

Product 1

HCID 69802498HCID 69802498, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.2 g (0.596 mmol) of (±)-cis-7-[(4-phenylpiperdin-1-yl)methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol dissolved in 5 ML THF were added dropwise to a suspension of 0.029 g (0.715 mmol) of NaH (60% dispersion in mineral oil) in 10 mL THF. After 30 min at room temperature, 0.12 mL of allyl bromide were added and the reaction mixture was refluxed 8 h. After cooling, the reaction mixture was quenched by addition of MeOH and the solvent was removed in vacuo. The residue was taken up in 1 N NaOH and extracted with CH2Cl2; the organic phase was dried and the solvent was removed in vacuo. The resulting crude product was purified by chromatography, eluting with a mixture CH2Cl2/MeOH 100:2 respectively, yielding an oil which was dissolved in Et2O; the solution was brought to acidic pH with Et2O/HCl and the solvent was removed in vacuo. The resulting solid was triturated with Et2O, yielding 65 mg of the title product. m.p. 126-128° C.

Workup

  1. temperaturethe reaction mixture was refluxed 8 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched by addition of MeOH
  4. customthe solvent was removed in vacuo
  5. extractionextracted with CH2Cl2
  6. customthe organic phase was dried
  7. customthe solvent was removed in vacuo
  8. customThe resulting crude product was purified by chromatography
  9. washeluting with a mixture CH2Cl2/MeOH 100:2 respectively
  10. customyielding an oil which
  11. customthe solvent was removed in vacuo
  12. customThe resulting solid was triturated with Et2O

Sources & evidence

ORD record
ord-53ab4c17a69d44548ca8bd3dcade4296
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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