Sodium Hydroxide → HCID 67637922, compound

HRID 467065Notes

Reaction equation

HRID 467065 reaction equation
[ClH:1].[CH2:2]([N:6]1[CH2:11][CH2:10][C@@H:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C@H:8]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)[CH2:7]1)[CH2:3][CH2:4][CH3:5].[Br:30]Br.[OH-].[Na+]>C(Cl)Cl>[ClH:1].[Br:30][C:26]1[CH:25]=[C:24]2[O:27][CH2:28][O:29][C:23]2=[CH:22][C:21]=1[O:20][CH2:19][C@H:8]1[C@H:9]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH2:10][CH2:11][N:6]([CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 69304204HCID 69304204, compound

Product 1

HCID 67637922HCID 67637922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(-)-trans-1-butyl-4-(4-fluorophenyI)-3-(3,4-methylenedioxyphenoxymethyl)-piperidine hydrochloride (1 g) was dissolved in CH2Cl2 (50 ml). Bromine (0.124 ml) was added dropwise at R.T. After stirring for 2 h aqueous NaOH was added, and the CH2Cl2 layer was isolated, dried over Na2SO4, filtered and evaporated to dryness. The residue was dissolved in acetone, excess conc. HCl was added and the above mentioned bromo compound was precipitated by addition of ether. M.p. 116° C.

Workup

  1. additionwas added
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in acetone
  6. additionexcess conc. HCl was added
  7. customwas precipitated by addition of ether

Sources & evidence

ORD record
ord-fabb8a1642b0443fb12d98de5640f65f
Source dataset
uspto-grants-1992_10
Patent number
US05158961

Reaction notes

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