Ethanol → HCID 85786838, compound

HRID 223567Notes

Reaction equation

HRID 223567 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9](C=O)[CH2:8][CH2:7]1)=O.Cl.[NH2:20][OH:21].C([O-])(=O)C.[NH4+].C(O)C>O>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4](=[N:20][OH:21])[CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 134508954-(2,4-Dichlorobenzoyl)piperidine-1-carbaldehyde

Product 1

HCID 85786838HCID 85786838, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 105 g of 4-(2,4-dichlorobenzoyl)-1-formylpiperidine, 70 g of hydroxylamine hydrochloride, 135 g of ammonium acetate, 1.05 l of ethanol and 350 ml of water was stirred and heated at 130° for 40 hrs. The reaction mixture was evaporated and 2.0 l of water was added to the residue. The water was decanted from the oil and the oil was washed two times with 500 ml of water and dissolved in about 400 ml of dichloromethane. The insoluble material was collected. The dichloromethane extract was washed twice with 600 ml of water. The combined aqueous phases were made basic with potassium carbonate/water. The precipitate was filtered, washed with water and dried over phosphorus pentoxide in vacuo to yield 27.2 g (9.96%) of 4-(2,4-dichlorobenzoyl)piperidine oxime. The insoluble material was dissolved in hot water and made alkaline with potassium carbonate-water. The precipitate was filtered, washed with water and dried over phosporus pentoxide in vacuo. The solid was dissolved in 200 ml methanol and 2 ml of conc hydrochloric acid was added. After heating for 5 mins, the solution was filtered and evaporated in vacuo to dryness. The residue was recrystallized from methanol-ether to yield product as the hydrochloride, mp 284°.

Workup

  1. temperatureheated at 130° for 40 hrs
  2. customThe reaction mixture was evaporated
  3. addition2.0 l of water was added to the residue
  4. customThe water was decanted from the oil
  5. washthe oil was washed two times with 500 ml of water
  6. dissolutiondissolved in about 400 ml of dichloromethane
  7. customThe insoluble material was collected
  8. extractionThe dichloromethane extract
  9. washwas washed twice with 600 ml of water
  10. filtrationThe precipitate was filtered
  11. washwashed with water
  12. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-85f1dae3df0e4c59a28b023ab1e7d2bd
Source dataset
uspto-grants-1982_10
Patent number
US04355037

Reaction notes

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