Pyridine → HCID 4419998, compound

HRID 1381699Notes

Reaction equation

HRID 1381699 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. A mixture of 200 g of N-(4-chlorophenylacetyl)piperidine, 94 g of phosphorous pentasulfide and 750 ml of pyridine was heated at reflux with vigorous stirring for 18 hours, then cooled and concentrated in vacuo. The residue was taken up in 1.8 liters of water, heated at 50° C. for 30 minutes, cooled and exhaustively extracted with ether. The ether extracts were combined, washed successively with water, 5% hydrochloric acid twice and saturated sodium chloride and dried. The solution was percolated through a bed of neutral alumina followed by elution with ether. The resulting oil was crystallized twice from methylcyclohexane, giving 100 g of N-(4-chlorophenylthioacetyl)piperidine as orange crystals, mp 82.5°-83.5° 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-2dd1d5dcd070444c8a6b84587a9d5ab5
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

Loading…