Hydrochloric Acid → Methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate dihydrochloride

HRID 1877780Notes

Reaction equation

HRID 1877780 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:20])([CH3:19])[CH2:5][N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.O1CCOCC1.[ClH:28]>C(O)(C)C>[ClH:28].[ClH:28].[CH3:19][C:4]([CH3:20])([CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[C:3]([O:2][CH3:1])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68155978Tert-butyl 4-(3-methoxy-2,2-dimethyl-3-oxopropyl)piperazine-1-carboxylate

Product 1

HCID 68155933Methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate dihydrochlorideYield 59%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of tert-butyl 4-(3-methoxy-2,2-dimethyl-3-oxopropyl)piperazine-1-carboxylate (58.0 g, 193.08 mmoles) in isopropyl alcohol (150 mL) add a 4M dioxane solution of hydrogen chloride ((4 equiv); 193.08 mL, 772.31 mmoles) over 15 minutes, observing gas evolution and a fine precipitate. Heat at 55° C. for 3 h to give a white precipitate. Cool to 10° C. and collect the white solid by filtration, wash with further isopropyl alcohol (30 mL), then EtOAc. Dry in a vacuum oven at 45° C. for 1 h to give methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate dihydrochloride (31 g, 59% yield). MS (m/z): =201.1 (M+1).

Workup

  1. customto give a white precipitate
  2. temperatureCool to 10° C.
  3. customcollect the white solid
  4. filtrationby filtration
  5. washwash with further isopropyl alcohol (30 mL)
  6. customDry in a vacuum oven at 45° C. for 1 h

Sources & evidence

ORD record
ord-c0c59c512d634641b120a18a56423c1b
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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