HCID 69067080, compound → HCID 69067830, compound

HRID 1912490Notes

Reaction equation

HRID 1912490 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C@H:15]([NH:19]C(=O)OC(C)(C)C)[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:29])[CH3:28])=[CH:4][CH:3]=1>O1CCOCC1>[ClH:1].[NH2:19][C@H:15]([CH:16]([CH3:18])[CH3:17])[C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]([CH3:28])([CH3:29])[CH2:10]1)=[O:27]

Participants

3

Reactant 1

HCID 69067080HCID 69067080, compound

Product 1

HCID 69067830HCID 69067830, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(4-chlorophenyl)-2,2-dimethylpiperazine (0.76 g, 3.38 mmol) in DMF (10 mL), was added (R)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (0.735 g, 3.38 mmol), BOP (1.496 g, 3.38 mmol) and DIPEA (0.588 mL, 3.38 mmol). The mixture was stirred at rt for 2 h, quenched with aq. NaHCO3, extracted with EtOAc, and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by a flash column chromatography using 30% EtOAc in hexanes as an eluent. The product containing fractions were concentrated and dried to give (R)-tert-butyl 1-(4-(4-chlorophenyl)-3,3-dimethylpiperazin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1.36 g, 3.21 mmol, 95% yield) as a yellow oil. To (R)-tert-butyl 1-(4-(4-chlorophenyl)-3,3-dimethylpiperazin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate was added 4N HCL in dioxane and the resulting mixture stirred at room temperature until the starting material had been consumed. The volatile solvents were removed and the product dried to give (R)-2-Amino-1-(4-(4-chlorophenyl)-3,3-dimethylpiperazin-1-yl)-3-methylbutan-1-one hydrochloride as a white solid.

Workup

  1. customhad been consumed
  2. customThe volatile solvents were removed
  3. customthe product dried

Sources & evidence

ORD record
ord-aabb260efc534578be2ca29ca5ad2185
Source dataset
uspto-grants-2013_12
Patent number
US08609664B2

Reaction notes

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