Hydrochloric Acid → HCID 18346049, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]([C@@H:15]([NH:19]C(OC(C)(C)C)=O)[CH:16]([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1>CO>[Cl:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]([C@@H:15]([NH2:19])[CH:16]([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
1 N ethereal hydrogen chloride solution (80 ml, 80 mmol) was added to a solution of 1(S)-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]-N-(tert-butoxycarbonyl)-2-methylpropylamine (4.28 g, 9.64 mmol) in methanol (50 ml) and the reaction mixture was heated at 70° C. After 2.5 h, the reaction mixture was concentrated and the solid was suspended in ether and filtered to give 1-(S)-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]-2-methylpropylamine as the bis hydrochloride salt. The product was dissolved in water, treated with triethylamine (4.0 ml, 28.9 mmol) and the free amine was extracted into ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated to give 1-(S)-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]-2-methylpropylamine (3.2 g) as the free amine.
Workup
- concentrationthe reaction mixture was concentrated
- filtrationfiltered
Sources & evidence
- ORD record
- ord-6f1beadfe4e0413aa73106b3dfc4ac11
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06683074B1
Reaction notes
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