Hydrochloric Acid → HCID 18346049, compound

HRID 1610886Notes

Reaction equation

HRID 1610886 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]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18346050HCID 18346050, compound

Product 1

HCID 18346049HCID 18346049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-yl carbonyl]-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

  1. concentrationthe reaction mixture was concentrated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-72dd7ad72aee46e59fa0e46a9b831088
Source dataset
uspto-grants-2006_01
Patent number
US06984637B2

Reaction notes

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