Hydrochloric Acid → Ammonia

HRID 1926673Notes

Reaction equation

HRID 1926673 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[NH3:9].[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 57682605HCID 57682605, compound

Product 2

HCID 222AmmoniaHCID 250638764-[(3-Bromophenyl)phenylmethyl]-1-piperazineacetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 2-(4-((3-bromophenyl)(phenyl)methyl)piperazin-1-yl)acetate (2.0 g, 4 mmol) in dioxane (10 mL) was added 4N HCl solution in 1,4-dioxane (30 mL, 823 mmol) followed by concentrated HCl (2.0 mL, 55 mmol). The reaction was stirred at 50° C. for 6 h and concentrated under vacuum. The crude product was purified by SCX column eluting with methanol then 2N NH3 in MeOH solution to give the title compound as a racemate (1.62 g, 93%). MS (ESI, pos. ion) m/z: 389.1 (M+).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe crude product was purified by SCX column
  3. washeluting with methanol

Sources & evidence

ORD record
ord-7de7ec683e714dee99d28cbc1ec1d528
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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