Acetic Acid → Piperidine, 1-methyl-4-phenyl-, hydrochloride

HRID 885833Notes

Reaction equation

HRID 885833 reaction equation
[ClH:1].[C:2]1([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:18](C)=O.[Na+].CC(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[ClH:1].[CH3:18][N:11]1[CH2:10][CH2:9][CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 825094-Phenylpiperidinium chlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 202390Piperidine, 1-methyl-4-phenyl-, hydrochlorideYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-phenyl piperidine hydrochloride (1.23 g, 6.2 mmol), formaldehyde (36.5% in H2O, 0.702 ml, 9.3 mmol), NaBH(OAc)3 (2.63 g, 12.42 mmol) and AcOH (0.71 ml, 12.42 mmol) in DCM (30 ml) was stirred for 24 hours at room temperature. The mixture was then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with DCM. The pooled organic phases were dried over Na2SO4 and evaporated to dryness. The residue was dissolved in DCM and treated with HCl in Et2O observing the precipitation of a white solid. The solid was filtered off through a Buchner funnel to obtain 1 g of 1-methyl-4-phenylpiperidine hydrochloride as a white solid.

Workup

  1. extractionextracted twice with DCM
  2. dry with materialThe pooled organic phases were dried over Na2SO4
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in DCM
  5. additiontreated with HCl in Et2O observing
  6. customthe precipitation of a white solid
  7. filtrationThe solid was filtered off through a Buchner funnel

Sources & evidence

ORD record
ord-71d06a0a7ee742258550f2b7f0666f99
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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