Hydrochloric Acid → 2-[[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]amino]-N-methylpyrimidine-4-carboxamide, hydrochloride

HRID 5340Notes

Reaction equation

HRID 5340 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]3[N:23]=[C:22]([C:24]([O:26]C)=O)[CH:21]=[CH:20][N:19]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[CH3:30][NH2:31].Cl>CC(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]3[N:23]=[C:22]([C:24]([NH:31][CH3:30])=[O:26])[CH:21]=[CH:20][N:19]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6329MethylamineHCID 19795859Methyl 2-[[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]amino]pyrimidine-4-carboxylate

Product 1

HCID 678721592-[[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]amino]-N-methylpyrimidine-4-carboxamide, hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.5 g (11.5 mmols) of methyl 2-[[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]amino]pyrimidine-4-carboxylate and 200 ml of methanol are introduced into a 0.5 l, round bottomed flask and then the solution is saturated with gaseous methylamine. The reaction mixture is stirred at room temperature while saturating several times with gaseous methylamine. The solvent is evaporated under reduced pressure. 4.05 g (10.4 mmols) of base are obtained to which 104 ml of 0.1N hydrochloric acid in 2-propanol are added. The solvent is evaporated and the product is recrystallised from 2-butanone. 3.8 g of compound are obtained.

Workup

  1. concentrationwhile saturating several times with gaseous methylamine
  2. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-4aeb686c490442b0b6a3ee76700a4b23
Source dataset
uspto-grants-1993_09
Patent number
US05244894

Reaction notes

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