Diisopropylethylamine → HCID 178487196, compound

HRID 1762584Notes

Reaction equation

HRID 1762584 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:8]([CH2:10]OS(C)(=O)=O)[C:7]=2[CH:16]=1.[OH2:17].Cl.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=O.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:8]([CH2:10][N:19]3[CH2:24][CH2:23][C:22](=[O:17])[CH2:21][CH2:20]3)[C:7]=2[CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22021827Piperidone monohydrate hydrochlorideHCID 178487221HCID 178487221, compound

Product 1

HCID 178487196HCID 178487196, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 12.11 g (50 mmol) of methanesulphonic acid (5-methoxybenzocyclobuten-1-ylmethyl) ester in 100 ml of dimethylformamide there are added first 8.45 g (55 mmol) of piperidone hydrochloride monohydrate and then 22.62 g (175 mmol) of N-ethyl-N,N-diisopropylamine. The mixture is stirred at 80° C. for 18 hours 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 at reduced temperature with sodium hydroxide solution and extracted with dichloromethane. The extracts 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) with toluene/ethyl acetate (1:1). 1-[(5-methoxybenzocyclobuten-1-yl)methyl]piperidin-4-one is obtained in the form of a light-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. extractionextracted 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) with toluene/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-cb9edf5a488d4e68926d25e35618d88b
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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