(2R,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol HCl → (Z)-(RS)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethylamine hydrochloride

HRID 2394979Notes

Reaction equation

HRID 2394979 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:19])[CH2:4][CH:5]([CH3:18])[C:6]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)(O)[CH2:7][CH3:8]>Cl>[ClH:1].[CH3:17][O:16][C:12]1[CH:11]=[C:10](/[C:6](=[CH:7]\[CH3:8])/[CH:5]([CH3:18])[CH2:4][N:3]([CH3:19])[CH3:2])[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 18974517(2R,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol HCl

Product 1

HCID 67662047(Z)-(RS)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethylamine hydrochlorideYield 42.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

200 g (0.69 mole) of hydrochloride (2) were dissolved in one litre of concentrated hydrochloric acid and allowed to stand at room temperature. The hydrochloric acid was removed by distillation under vacuum. The residue was dissolved in 1 l of ice-water and the pH was adjusted to 13 with 10 molar sodium hydroxide solution. After extraction with ether, drying the organic phase and removing the solvent by distillation, 162 g of crude product were obtained, and were purified by recrystallisation. 79 g (42% theoretical) of hydrochloride (1) with a melting point of 169°-170° C. were obtained.

Workup

  1. customto stand at room temperature
  2. customThe hydrochloric acid was removed by distillation under vacuum
  3. dissolutionThe residue was dissolved in 1 l of ice-water
  4. extractionAfter extraction with ether
  5. customdrying the organic phase
  6. customremoving the solvent
  7. distillationby distillation
  8. custom162 g of crude product were obtained
  9. customwere purified by recrystallisation

Sources & evidence

ORD record
ord-91112e3c564546939c0e202761c1d68f
Source dataset
uspto-grants-1998_09
Patent number
US05811582

Reaction notes

Loading…