Hydrochloric Acid → Imipramine

HRID 335046Notes

Reaction equation

HRID 335046 reaction equation
OC1C(C(O)=O)=CC2C(C=1)=CC=CC=2.Cl.[OH-].[Na+].[CH3:18][N:19]([CH2:21][CH2:22][CH2:23][N:24]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:32][CH2:31][C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]1=2)[CH3:20].Cl>O>[CH3:18][N:19]([CH2:21][CH2:22][CH2:23][N:24]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=2[CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]1=2)[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 71043-Hydroxy-2-naphthoic acidHCID 8228Imipramine Hydrochloride2×HCID 14798Sodium Hydroxide2×

Product 1

HCID 3696ImipramineYield 105.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution containing 7.7 g of 3-hydroxy-2-napthoic acid in 75.0 g of USP water was added as necessary dilute HCl or NaOH solution to adjust the solution to about pH 9.4. To a second solution of 13.6 g of imipramine HCl in 100.0 g of USP water was added as necessary dilute HCl or NaOH solution to adjust the solution to about pH 4.5. The imipramine HCl solution was added to the 3-hydroxy-2-napthoic sodium salt solution over a period of about 2 h. The mixture was stirred and held at around 50° C. for approximately 18 h. The mixture was cooled to below about 25° C. and the solids were collected by filtration. The solid cake was washed with USP water (2×100 g). The solid cake was dried at about 105° C. under vacuum to yield a powder (12.7 g) and characterized by DSC (FIG. 13), FTIR (FIG. 14) and 1H NMR (FIG. 15).

Workup

  1. temperatureThe mixture was cooled to below about 25° C.
  2. filtrationthe solids were collected by filtration
  3. washThe solid cake was washed with USP water (2×100 g)
  4. customThe solid cake was dried at about 105° C. under vacuum

Sources & evidence

ORD record
ord-28456e8ed5094c7dbca468cfb73f22f7
Source dataset
uspto-grants-2014_11
Patent number
US08883863B1

Reaction notes

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