Diisopropylethylamine → 1-[2-(Chroman-3-yl)ethyl]-4-oxopiperidine

HRID 1032419Notes

Reaction equation

HRID 1032419 reaction equation
[OH2:1].Cl.[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.C(N(C(C)C)C(C)C)C.C1(C)C=CC(S(O[CH2:29][CH2:30][CH:31]2[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[O:33][CH2:32]2)(=O)=O)=CC=1>CN(C)C=O>[O:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:40][CH:31]([CH2:30][CH2:29][N:3]2[CH2:8][CH2:7][C:6](=[O:1])[CH2:5][CH2:4]2)[CH2:32]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 148384153-[2-(p-Toluenesulphonyloxy)ethyl]chromanHCID 22021827Piperidone monohydrate hydrochloride

Product 1

HCID 148384511-[2-(Chroman-3-yl)ethyl]-4-oxopiperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First 8.45 g (55 mmol) of piperidone hydrochloride monohydrate and then 22.62 g (175 mmol) of N-ethyl-N,N-diisopropylamine are added to a solution of 16.62 g (50 mmol) of 3-[2-(p-toluenesulphonyloxy)ethyl]chroman in 100 ml of dimethylformamide. The mixture is stirred for 18 hours at 80° and, after cooling, is concentrated to dryness by evaporation under reduced pressure. The residue is dissolved in diethyl ether and washed with water. The organic phase is separated off and extracted with 2N hydrochloric acid. The hydrochloric acid extracts are combined, rendered alkaline, while cold, with concentrated sodium hydroxide solution and extracted with dichloromethane. The dichloromethane phases are combined, dried over sodium sulphate and concentrated to dryness by evaporation under reduced pressure. A dark brown resin is obtained which is purified by chromatography on 350 g of silica gel (0.040-0.063 mm) using toluene/ethyl acetate (1:1) as the eluant. 1-[2-(chroman-3-yl)ethyl]-4-oxopiperidine is obtained in the form of a pale yellow oil.

Workup

  1. temperatureafter cooling
  2. concentrationis concentrated to dryness by evaporation under reduced pressure
  3. dissolutionThe residue is dissolved in diethyl ether
  4. washwashed with water
  5. customThe organic phase is separated off
  6. extractionextracted with 2N hydrochloric acid
  7. extractionwhile cold, with concentrated sodium hydroxide solution and extracted with dichloromethane
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated to dryness by evaporation under reduced pressure
  10. customA dark brown resin is obtained which
  11. customis purified by chromatography on 350 g of silica gel (0.040-0.063 mm)

Sources & evidence

ORD record
ord-171ca622a9724f2b84892ef823110e9c
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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