Hydrochloric Acid → HCID 22165608, compound

HRID 1032347Notes

Reaction equation

HRID 1032347 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23](C2CCCNC2)[CH:24]=[CH:25][CH:26]=1.C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C.Cl.[CH2:41](Cl)Cl>O>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH2:9][C:10]([N:35]2[CH2:36][CH2:37][CH2:41][CH:39]([C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:20][CH3:19])[CH2:38]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 110742303-(3-Methoxyphenyl)piperidineHCID 131111942-(Diphenylmethoxy)acetyl chloride

Product 1

HCID 22165608HCID 22165608, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.8 g (10.9 mmole) of (diphenylmethoxy) acetyl chloride in 25 cm3 of methylene chloride was added quickly to a solution of 2.1 g (10.9 mmole) of (3-(3-methoxyphenyl) piperidine [prepared using the B. M. Iselin and K. Hoffmann method, Helv. Chim. Acta 1954, 37, 178] and 2.2 g (21.8 mmole) of triethylamine in 75 cm3 of methylene chloride. The solution was brought to reflux and maintained at reflux for 10 hours, then poured into a solution of 10cm3 of hydrochloric acid in 300 cm3 of water. The mixture was extracted with methylene chloride, washed with water and dried on sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified using silica gel chromatography (eluent,hexane-ethyl acetate, 1/1). There was obtained 3.3 g (yield: 73%) of 1-[(diphenylmethoxy)acetyl]-3-(methoxyphenyl)piperidine.

Workup

  1. customprepared
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux for 10 hours
  5. extractionThe mixture was extracted with methylene chloride
  6. washwashed with water
  7. customdried on sodium sulfate
  8. customAfter the solvent was evaporated under reduced pressure
  9. customthe residue was purified

Sources & evidence

ORD record
ord-47a90cf2b40f4cbf9d5ebe0bb2f160e1
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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