Nefazodone → Nefazodone Hydrochloride

HRID 1636233

Reaction equation

HRID 1636233 reaction equation
[CH3:1][CH2:2][C:3]1[N:8]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:6](=[O:7])[N:5]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[CH:29][CH:30]=[C:31]([Cl:33])[CH:32]=3)[CH2:23][CH2:22]2)[N:4]=1.[OH-].[Na+]>O>[CH3:1][CH2:2][C:3]1[N:8]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:6](=[O:7])[N:5]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[CH:29][CH:30]=[C:31]([Cl:33])[CH:32]=3)[CH2:23][CH2:22]2)[N:4]=1.[ClH:33]

Participants

4

Reactant 2

HCID 4449NefazodoneHCID 14798Sodium Hydroxide

Product 1

HCID 54911Nefazodone Hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
42.5 °C

Procedure

Nefazodone HCl was prepared in accordance with Example 2 of U.S. Pat. No. 4,338,317. Nefazodone HCI was dissolved in water with gentle heating (40-45° C.). An equimolar quantity of sodium hydroxide solution (0.1 N) was added with constant stirring while cooling with ice. Nefazodone base precipitated as a sticky gum which was separated and washed repeatedly with water. The base was washed with water until no chloride ions (AgNO3 test) were detected in the washings. Nefazodone base was then dissolved and crystallized from isopropyl alcohol (IPA) to give a solid melting 81-83° C.

Workup

  1. temperaturewhile cooling with ice
  2. customNefazodone base precipitated as a sticky gum which
  3. customwas separated
  4. washwashed repeatedly with water
  5. washThe base was washed with water until no chloride ions (AgNO3 test)
  6. dissolutionNefazodone base was then dissolved
  7. customcrystallized from isopropyl alcohol (IPA)
  8. customto give a solid
  9. custommelting 81-83° C.

Sources & evidence

ORD record
ord-02174f92564844058b99dde18f2e5844
Source dataset
uspto-grants-2000_03
Patent number
US06034085

Linked notes

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