Trimethyl orthoformate → 4,4-Dimethoxypiperidine

HRID 1602089Notes

Reaction equation

HRID 1602089 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7]C(=O)[CH2:5][CH2:4]1.[CH:10](OC)([O:13][CH3:14])[O:11][CH3:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:12][O:11][C:10]1([O:13][CH3:14])[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2723901Piperonylamine

Product 1

HCID 5574694,4-Dimethoxypiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 9 ml of methanol were dissolved 0.69 g of 4-piperidone hydrochloride monohydrate, 0.74 ml of trimethyl orthoformate and 86 mg of p-toluenesulfonic acid monohydrate, and the reaction was conducted at room temperature for 24 hours. The reaction mixture was evaporated under reduced pressure to remove the solvent. The residue was dissolved into 2 ml of N,N-dimethylacetamide and admixed with 1.4 ml of triethylamine to give a solution of 4,4-dimethoxypiperidine.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto remove the solvent
  3. dissolutionThe residue was dissolved into 2 ml of N,N-dimethylacetamide

Sources & evidence

ORD record
ord-a9f177263f9d43879d3ff0225fa863ad
Source dataset
uspto-grants-1999_11
Patent number
US05981522

Reaction notes

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