Hydrochloric Acid → gamma-(4-Benzyl-4-hydroxypiperidino)-2-chlorobutyrophenone hydrochloride

HRID 26175Notes

Reaction equation

HRID 26175 reaction equation
[CH2:1]([C:8]1([OH:26])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16](N)[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].[ClH:31]>O>[ClH:31].[CH2:1]([C:8]1([OH:26])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]([Cl:31])[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21324676gamma-(4-Benzyl-4-hydroxypiperidino)-2-aminobutyrophenoneHCID 23668193Sodium Nitrite

Product 1

HCID 86736453gamma-(4-Benzyl-4-hydroxypiperidino)-2-chlorobutyrophenone hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled solution of 3.6 g of γ-(4-benzyl-4-hydroxypiperidino)-2-aminobutyrophenone in 35 ml of 2N hydrochloric acid was added dropwise a solution of 0.74 g of sodium nitrite in 5 ml of water with stirring below 0° C. The resulting diazonium salt solution was added all at once to a cold suspension of 1.5 g of cuprous chloride in 5 ml of concentrated hydrochloric acid with vigorous stirring. The mixture was stirred for 30 minutes under cooling with ice, and stirring was continued for 2 hours at room temperature and then for 1 hour at 55°-60° C. After cooling, the reaction mixture was made alkaline, and extracted with chloroform. The extract was washed with water, dried and concentrated to a residue. The residue was treated with methanolic hydrogen chloride and recrystallization of the resulting solid matter from isopropanol gave γ-(4-benzyl-4-hydroxypiperidino)-2-chlorobutyrophenone hydrochloride.8c

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. temperatureunder cooling with ice
  3. stirringstirring
  4. waitfor 1 hour at 55°-60° C
  5. temperatureAfter cooling
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated to a residue
  10. additionThe residue was treated with methanolic hydrogen chloride and recrystallization of the resulting solid matter from isopropanol

Sources & evidence

ORD record
ord-72b3ad87da5a47c7958a2a715a962bb0
Source dataset
uspto-grants-1979_04
Patent number
US04148796

Reaction notes

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