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1-Bromo-4-fluorobenzene → alpha,alpha-Bis(4-fluorophenyl)-1-(phenylmethyl)-4-piperidinemethanol

HRID 484714
Notes
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Reaction equation

HRID 484714 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].[C:10]1([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]([O:25]CC)=O)[CH2:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=2)([CH:20]2[CH2:19][CH2:18][N:17]([CH2:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:22][CH2:21]2)[OH:25])=[CH:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 5462224Magnesium

Product 1

HCID 13519964alpha,alpha-Bis(4-fluorophenyl)-1-(phenylmethyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a stirred and refluxing Grignard-complex, previously prepared starting from 70 parts of 1-bromo-4-fluorobenzene and 10 parts of magnesium in 270 parts of tetrahydrofuran, was added dropwise a solution of 25 parts of ethyl 1-(phenylmethyl)-4-piperidinecarboxylate in 90 parts of tetrahydrofuran. Upon completion, stirring was continued for 2 hours at reflux temperature. The reaction mixture was cooled and poured onto a saturate ammonium chloride solution. The organic phase was separated, dried, filtered and evaporated, yielding 40 parts of α,α-bis(4-fluorophenyl)-1-(phenylmethyl)-4-piperidinemethanol as a residue (intermediate 12).

Workup

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux temperature
  5. temperatureThe reaction mixture was cooled
  6. customThe organic phase was separated
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-aec277b26be646beadca3c33e69ff98d
Source dataset
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04533665

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes