ChemicalBook CAS DataBase List IMIPRAMINE

IMIPRAMINE synthesis

12synthesis methods

Product Name:IMIPRAMINE
CAS Number:50-49-7
Molecular formula:C19H24N2
Molecular Weight:280.41

Imipramine, 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f] azepine (7.1.1), is synthesized by the alkylation of 10,11-dihydro-5H-dibenz[b,f]azepine using 3-dimethylaminopropylchloride in the presence of sodium amide [1–3].

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Yield:-

Reaction Conditions:

with sodium hydroxide in water

Steps:

1 EXAMPLE 1
Preparation Of Imipramine Pamoate
EXAMPLE 1
To a slurry of Pamoic acid (32.4 g) in ethyl acetate (250 mL) in a clean round bottomed flask, Imipramine (85 g, pre-generated from Imipramine hydrochloride -90 g, sodium hydroxide -18 kg in water, 60 -100 mL) solution in ethyl acetate is added maintaining the temperature below 50° C. for 3-4 h.
After complete addition, the reaction mixture is stirred at room temperature for about 12-14 h.
The bright yellow slurry thus obtained is filtered and washed with ethyl acetate (400 mL) and dried to get Imipramine Pamoate (76 g, 96%) as bright yellow crystalline product.

References:

R L Fine Chem;RAMESHA, Andagar Ramakrishna;ROY, Anjan Kumar US2015/225349, 2015, A1 Location in patent:Paragraph 0034

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494-19-9 Synthesis