1,1-Dichloroethane → 4-(4-Methoxyphenyl)piperidine

HRID 1417817Notes

Reaction equation

HRID 1417817 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(Cl)C.ClC(OC(Cl)=O)C>>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 232889401-Benzyl-4-(4-methoxyphenyl)piperidine

Product 1

HCID 106792704-(4-Methoxyphenyl)piperidine

Procedure

A mixture of 1-benzyl-4-(4-methoxy)phenylpiperidine (XVIII, Step 3, 0.4724 g, 1.7 mmol), dichloroethane (4.4 ml) and 1-chloroethylchloroformate (0.66 ml, 6.1 mmol) is refluxed overnight, then concentrated and the residue refluxed in methanol for 2 hours. After cooling, the solvent is removed and the resulting solids are slurried in dichloromethane. Ether is added and the solids are collected and then partitioned between dichloromethane and saturated sodium bicarbonate. The combined organic phases are backwashed with saline, dried over magnesium sulfate, and concentrated to give a residue which is chromatographed on silica gel eluting with methanol/dichloromethane (4/96) containing ammonium hydroxide (0.4%), followed by methanol/dichloromethane (6/94) containing ammonium hydroxide (0.4%). The appropriate fractions are pooled and concentrated to give 4-(4-methoxyphenyl)piperidine (XIX), NMR (CDCl3) 1.66, 1.83, 2.06, 2.58, 2.76, 3.21, 3.79, 6.85 and 7.15 δ.

Workup

  1. temperatureis refluxed overnight
  2. concentrationconcentrated
  3. temperaturethe residue refluxed in methanol for 2 hours
  4. temperatureAfter cooling
  5. customthe solvent is removed
  6. additionEther is added
  7. customthe solids are collected
  8. custompartitioned between dichloromethane and saturated sodium bicarbonate
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customto give a residue which
  12. customis chromatographed on silica gel eluting with methanol/dichloromethane (4/96)
  13. additioncontaining ammonium hydroxide (0.4%)
  14. additioncontaining ammonium hydroxide (0.4%)
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-672fd119708d49958a53cf41542a00da
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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