Hydrochloric Acid → 1-[(Diphenylmethoxy)acetyl]-3-phenylpiperidine

HRID 1032344Notes

Reaction equation

HRID 1032344 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.[C:19]1([CH:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.Cl>C(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:27]2[CH2:28][CH2:29][CH2:30][CH:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1072073-PhenylpiperidineHCID 13111194(Diphenylmethoxy) acetyl chloride

Product 1

HCID 145563271-[(Diphenylmethoxy)acetyl]-3-phenylpiperidineYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.5 g (17.2 mmole) of (diphenylmethoxy) acetyl chloride in 50 cm3 of methylene chloride was added drop-wise at room temperature to a solution of 2.8 g (17.2 mmole) of 3-phenylpiperidine [prepared according to M. Julia et al., Bull. Soc. Chim. Fr. 1968, 987] and 3.5 g (34.4 mmole) of triethylamine in 100 cm3 of methylene chloride. The reaction mixture was heated to reflux for 4 hours; it was allowed to stand overnight and was then poured into a solution of 10 cm3 of concentrated 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 by silica gel filtration (eluent, hexaneethyl acetate, 1/1), then by recrystallization from a hexane-ethyl acetate mixture. There was obtained 4.3 g (yield: 65%) of 1-[(diphenylmethoxy)acetyl]-3-phenylpiperidine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. extractionThe mixture was extracted with methylene chloride
  4. washwashed with water
  5. customdried on sodium sulfate
  6. customAfter the solvent was evaporated under reduced pressure
  7. filtrationthe residue was purified by silica gel filtration (eluent, hexaneethyl acetate, 1/1)
  8. customby recrystallization from a hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-93aaf05872ae490a9d9e9749bfb780d3
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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