Hydrochloric Acid → 1-(trans-4-Aminomethyl-L-Prolyl)-4-(3-Chloro-2-Methylphenyl)piperazine Dihydrochloride

HRID 2185470Notes

Reaction equation

HRID 2185470 reaction equation
[ClH:1].C(OC([NH:9][CH2:10][C@H:11]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:32]=3[CH3:38])[CH2:27][CH2:26]2)=[O:24])[CH2:12]1)=O)(C)(C)C>O1CCOCC1>[ClH:37].[ClH:1].[NH2:9][CH2:10][C@H:11]1[CH2:15][NH:14][C@H:13]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:32]=3[CH3:38])[CH2:27][CH2:26]2)=[O:24])[CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 540742211-[trans-4-(n-Tert-butoxycarbonylaminomethyl)-n-tert-butoxycarbonyl-l-prolyl]-4-(3-chloro-2-methylphenyl)piperazine

Product 1

HCID 701753811-(trans-4-Aminomethyl-L-Prolyl)-4-(3-Chloro-2-Methylphenyl)piperazine Dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (3 mL) was added to a solution of 1-[trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-L-prolyl]-4-(3-chloro-2-methylphenyl)piperazine (B, 98 mg) in 1,4-dioxane (3 mL) at room temperature. After stirring at room temperature for 20 min, the reaction mixture was concentrated in vacuo. The residue was washed with ether to give the titled compound (61 mg) as a white powder: 1H NMR (400 MHz, ) δ 2.37 (s, 3H), 2.40-2.47 (br s, 2H), 2.83 (br s, 1H), 3.07 (br s, 4H), 3.32 (br s, 3H), 3.77 (m, 5H), 5.02 (br s, 1H), 7.09 (m, 1H), and 7.25 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washThe residue was washed with ether

Sources & evidence

ORD record
ord-6aedb950e120433ea5b5b9d0cb3e263c
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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