HCID 18407068, compound → HCID 18407060, compound

HRID 1016495Notes

Reaction equation

HRID 1016495 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Br:21])[CH2:10][CH2:9]1)=O)(C)(C)C.[H][H]>C(OCC)(=O)C.C(O)C.O=[Pt]=O>[Br:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

6

Reactant 2

HCID 18407068HCID 18407068, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 18407060HCID 18407060, compoundYield 260%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(tert-butoxycarbonyl)-4-[(2-bromophenyl)methylene]-piperidine (XI, 8 g, 22.7 mmole) in ethyl acetate (75 ml) and ethanol (75 ml) was shaken with PtO2 (0.75 g) and hydrogen (60 psi) for 15 min. Two further batches of 1-(tert-butoxycarbonyl)-4-[(2-bromophenyl)-methylene]-piperidine (8 g each, 24 g total) were similarly reduced and the mixtures were filtered. The filtrates were combined and concentrated in vacuo. The residue (X) was dissolved in dioxane (200 ml) and 3N HCl (100 ml) and stirred for 18 hr. The solution was concentrated in vacuo and the residue was made basic with 50% sodium hydroxide. The mixture was extracted with CH2Cl2. The extracts were dried over Na2SO4 and concentrated in vacuo to give a yellow oil that was purified by short path vacuum distillation to give 4-(2-bromobenzyl)piperidine (VI) as a oil (15 g, 86.6%). The oil converted to the fumarate salt using fumaric acid (6.85 g) in 2-propanol to give 4-(2-bromobenzyl)piperidine fumarate as a white solid (15.8 g, 62.6% overall, mp: 164-165° C.).

Workup

  1. filtrationthe mixtures were filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue (X) was dissolved in dioxane (200 ml)
  4. concentrationThe solution was concentrated in vacuo
  5. extractionThe mixture was extracted with CH2Cl2
  6. dry with materialThe extracts were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil that
  9. distillationwas purified by short path vacuum distillation

Sources & evidence

ORD record
ord-8cc604d5b2da4970835f157058e97fcb
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

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