Ammonia → HCID 19908331, compound

HRID 1534806Notes

Reaction equation

HRID 1534806 reaction equation
[CH3:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)[CH2:6][CH:5]([CH3:16])[CH2:4][NH:3]1.Br.N>C(O)(=O)C>[CH3:1][CH:2]1[CH:7]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[CH2:6][CH:5]([CH3:16])[CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen Bromide2×HCID 19908330HCID 19908330, compound

Product 1

HCID 19908331HCID 19908331, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
95 °C

Procedure

A solution of 2.2 g (10 mmol) of 2,5-dimethyl-3-(4-methoxyphenyl)piperidine in 15 ml of a 45% solution of hydrogen bromide in acetic acid was heated at 95° C. for 1 hour. After the addition of another 5 ml of the 45% solution of hydrogen bromide in acetic acid the mixture was heated at 95° C. for a further 90 minutes. After cooling, the reaction mixture was poured on ice, rendered basic with concentrated ammonia and extracted twice with dichloromethane. The organic layer was dried on sodium sulphate, filtered and evaporated under reduced pressure. In this manner 1.7 g (83%) of substantially pure 2,5-dimethyl-3-(4-hydroxyphenyl)piperidine were obtained.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured on ice
  3. extractionextracted twice with dichloromethane
  4. customThe organic layer was dried on sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9ff54bf37eb043c8aa464a8a1e18cffc
Source dataset
uspto-grants-1992_02
Patent number
US05091393

Reaction notes

Loading…