Hydrochloric Acid → (R)-1-Isopropyl-3-methyl-piperazine

HRID 879601Notes

Reaction equation

HRID 879601 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH3:17])(OC(C)(C)C)=O.Cl>O1CCOCC1>[CH:14]([N:11]1[CH2:12][CH2:13][NH:8][C@H:9]([CH3:17])[CH2:10]1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86700416(R)-1-Boc-2-methyl-4-isopropylpiperazine

Product 1

HCID 59341019(R)-1-Isopropyl-3-methyl-piperazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To crude (R)-1-Boc-2-methyl-4-isopropylpiperazine in 1,4-dioxane (10 mL) was added HCl (5 mL of a 4M solution in 1,4-dioxane). The reaction mixture was stirred at room temperature for 28 h then concentrated. The resulting solid was suspended in diethyl ether, concentrated and dried on high vacuum for 1 d. The resulting solid was taken up in aq. 2N NaOH and the solution extracted three times with DCM. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to provide the free base of the product which was used without further purification. LCMS-ESI+: calc'd for C8H18N2 (M+H+): 143.1; Found: 143.7 (M+H+).

Workup

  1. concentrationthen concentrated
  2. concentrationconcentrated
  3. customdried on high vacuum for 1 d
  4. extractionthe solution extracted three times with DCM
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto provide the free base of the product which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-b937375b58724e5e83021def5109bbe7
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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