Pyridine → HCID 4419998, compound

HRID 2073357Notes

Reaction equation

HRID 2073357 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCCC1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](Cl)=[O:22])=[CH:16][CH:15]=1>CCOCC.O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:22])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 8082PiperidineHCID 906924-Chlorophenylacetyl chloride

Product 1

HCID 4419998HCID 4419998, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 120 g of dry pyridine, 103.2 g of piperidine and 1.5 liters of dry ether was stirred vigorously as 215.7 g of freshly distilled 4-chlorophenyl acetyl chloride in 250 ml of ether was added dropwise. After 4 hours the mixture was diluted with one liter of water and the organic phase collected. The aqueous phase was extracted with ether and the ether phases were combined, washed successively with 0.1N hydrochloric acid twice, 5% sodium hydroxide twice, saturated sodium chloride twice, dried and concentrated in vacuo. The residual oil was taken up in dichloromethane and percolated through a bed of neutral alumina with additional solvent. The resulting oil was crystallized from carbon tetrachloride:hexane (1:9), giving 243 g of N-(4-chlorophenylacetyl)piperidine as yellow crystals, mp 85°-85.5° C.

Workup

  1. additionwas added dropwise
  2. customthe organic phase collected
  3. extractionThe aqueous phase was extracted with ether
  4. washwashed successively with 0.1N hydrochloric acid twice
  5. dry with material5% sodium hydroxide twice, saturated sodium chloride twice, dried
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was crystallized from carbon tetrachloride:hexane (1:9)

Sources & evidence

ORD record
ord-ed3f3e1753d94537884a3263558a7857
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

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