Imipramine → CID 16052002

HRID 2237401Notes

Reaction equation

HRID 2237401 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH3:3].[CH:22]1[CH:27]=[C:26]2[CH:28]=[C:29]([C:48]([OH:50])=[O:49])[C:30]([OH:47])=[C:31]([CH2:32][C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[C:35]([C:43]([OH:45])=[O:44])[C:34]=3[OH:46])[C:25]2=[CH:24][CH:23]=1.[Na+].[CH3:52][N:53]([CH2:55][CH2:56][CH2:57][N:58]1[C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][C:67]=2[CH2:66][CH2:65][C:64]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]1=2)[CH3:54].[ClH:73]>O>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]1=2)[CH3:3].[ClH:73].[CH3:52][N:53]([CH2:55][CH2:56][CH2:57][N:58]1[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][C:64]=2[CH2:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][C:68]1=2)[CH3:54].[CH:22]1[CH:23]=[CH:24][C:25]2[C:26](=[CH:28][C:29]([C:48]([OH:50])=[O:49])=[C:30]([OH:47])[C:31]=2[CH2:32][C:33]2[C:34]([OH:46])=[C:35]([C:43]([OH:45])=[O:44])[CH:36]=[C:37]3[C:42]=2[CH:41]=[CH:40][CH:39]=[CH:38]3)[CH:27]=1

Participants

6

Reactant 3

HCID 3696ImipramineHCID 8228Imipramine HydrochlorideHCID 10179807Disodium methylenebis(2-hydroxy-3-naphthoate)2×

Product 2

HCID 8228Imipramine HydrochlorideHCID 16052002CID 16052002Yield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
41 °C

Procedure

Synthesis of Imipramine Pamaote—(Form VI)— A solution of disodium pamoate (43.88 g) in water (446.0 g) was prepared at a pH of about 9.5. A solution of imipramine HCl (63.38 g) in water (485.0 g) was prepared at a pH of about 4.0. The imipramine HCl solution (552.7 g) was added to the disodium pamoate solution at a controlled rate over a period of about 2.5 hours. After complete addition, the mixture was warmed to near 40-42° C. over approximately 4 h. Stirring was continued for approximately 3 additional hours at near 40-42° C. and then the solid product was isolated by filtration and washed with water. Imipramine pamoate (85.22 g) (92.6%) was isolated after drying at (78-80° C.). Throughout the heating process, samples were taken from the mixture and washed with water then dried. The Imipramine pamoate samples isolated at 42° C. (1.25 h) and 42° C. (2.25 h) contained a mixture of amorphous Imipramine Pamoate and Form VI. The Imipramine pamoate solid was characterized by PXRD (FIG. 18), FTIR (FIG. 19) and DSC (FIG. 20).

Workup

  1. customwas prepared at a pH of about 9.5
  2. additionAfter complete addition
  3. customwas continued for approximately 3 additional hours at near 40-42° C.
  4. customthe solid product was isolated by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-b1274ce3929140379cee41298b9f76a1
Source dataset
uspto-grants-2010_05
Patent number
US07718649B1

Reaction notes

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