3,5-Dimethylpiperidine → HCID 19864356, compound

HRID 2290174Notes

Reaction equation

HRID 2290174 reaction equation
Br[CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[O:4]1.[CH3:15][CH:16]1[CH2:21][CH:20]([CH3:22])[CH2:19][NH:18][CH2:17]1>C(OCC)(=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH:5]2[CH2:6][CH2:7][CH:3]([CH2:2][N:18]3[CH2:19][CH:20]([CH3:22])[CH2:21][CH:16]([CH3:15])[CH2:17]3)[O:4]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 1182593,5-DimethylpiperidineHCID 13563467HCID 13563467, compound

Product 1

HCID 19864356HCID 19864356, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

20 g (0.073 mole) of 2-bromomethyl-5-(4-chlorophenyl)-tetrahydrofuran and 25 g (0.22 mole) of 3,5-dimethylpiperidine are heated at 120° C. for 16 hours. The cooled reaction mixture is taken up in ethyl acetate and the mixture is washed twice with water, dried over sodium sulphate and concentrated in vacuo. The oily residue is purified by column chromatography (silica gel 60/ligroin-ethyl acetate 2:1/ethyl acetate). 4.5 g (20% of theory) of 2-(4-chlorophenyl)-5-(3,5-dimethylpiperidin-1-ylmethyl)-tetrahydrofuran are obtained as an oil; nD20 =1.5159.

Workup

  1. customThe cooled reaction mixture
  2. washthe mixture is washed twice with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue is purified by column chromatography (silica gel 60/ligroin-ethyl acetate 2:1/ethyl acetate)

Sources & evidence

ORD record
ord-4c6b26187b064d089dc2edeb97056827
Source dataset
uspto-grants-1986_10
Patent number
US04615725

Reaction notes

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