Imipramine Hydrochloride → HCID 178483497, compound

HRID 2035405

Reaction equation

HRID 2035405 reaction equation
[C:1]([O-:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Na+].[CH3:12][N:13]([CH2:15][CH2:16][CH2:17][N:18]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH2:26][CH2:25][C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=2)[CH3:14].Cl>O>[CH3:12][N:13]([CH2:15][CH2:16][CH2:17][N:18]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=2[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]1=2)[CH3:14].[C:1]([O-:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

4

Reactant 2

HCID 8228Imipramine Hydrochloride3×HCID 16760658Sodium Salicylate2×

Product 1

HCID 178483497HCID 178483497, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
62 °C

Procedure

Sodium Salicylate (16.4 g) in USP water (118.0 g) was stirred at 20° C. in a 1 L reactor. After 15 min, the solution was checked and exhibited pH 6.23. In a Imipramine HCl (31.7 g) in USP water (320.0 g) was stirred at 22° C. in a 500 mL reactor until a solution was observed (>20 min). The Imipramine HCl solution was checked and exhibited a pH 4.54. The Imipramine HCl solution was added via metered addition funnel to the sodium salicylate solution at 20° C. over 1.75 h. The reactor and addition funnel was rinsed to the reaction with USP water (20.0 g). The reaction mixture was heated from about 20° C. to about 50° C. for 1.2 h. The mixture was heated to about 62° C. for 17 h. Solids were collected by filtration of the mixture at 50° C. Residue was rinsed from the reactor to the filter with USP water (4×110.0 g). After drying on the filter for 1 h, solids were dried at about 65° C. to about 78° C. for approximately a day. Imipramine salicylate, mp 141-143.6° C. (39.8 g, 95.1%). Recrystallization of imipramine salicylate from a solution of ethanol-water (98/2) provided solid, mp 142.2-144.2° C. The DSC thermogram (FIG. 16), FTIR analysis (FIG. 17) and 1H NMR spectra (FIG. 18) were consistent with the expected structure.

Workup

  1. custom(>20 min)
  2. additionThe reactor and addition funnel
  3. washwas rinsed to the reaction with USP water (20.0 g)
  4. temperatureThe reaction mixture was heated from about 20° C. to about 50° C. for 1.2 h
  5. filtrationSolids were collected by filtration of the mixture at 50° C
  6. washResidue was rinsed from the reactor to the
  7. filtrationfilter with USP water (4×110.0 g)
  8. customAfter drying on the
  9. filtrationfilter for 1 h
  10. customsolids were dried at about 65° C. to about 78° C. for approximately a day
  11. customRecrystallization of imipramine salicylate from a solution of ethanol-water (98/2)
  12. customprovided solid, mp 142.2-144.2° C

Sources & evidence

ORD record
ord-7d323cbdd0da4c72beaeae6ecabf681f
Source dataset
uspto-grants-2013_11
Patent number
US08575151B1

Linked notes

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