Diisopropylethylamine → 4-(2,3-Dichloro-pyridin-4-yl)-2,2-dimethyl-1-phenyl-piperazine

HRID 587641Notes

Reaction equation

HRID 587641 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:10][C:11]1([CH3:23])[CH2:16][NH:15][CH2:14][CH2:13][N:12]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C>CC#N>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([N:15]2[CH2:14][CH2:13][N:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]([CH3:23])([CH3:10])[CH2:16]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 186285422,2-Dimethyl-1-phenylpiperazineHCID 448870382,3-Dichloro-4-iodopyridine

Product 1

HCID 574596184-(2,3-Dichloro-pyridin-4-yl)-2,2-dimethyl-1-phenyl-piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of D10 (1.083 g, 3.955 mmol), 2,2-dimethyl-1-phenylpiperazine (0.903 g, 4.745 mmol) [C.A.S. 2946-75-0] and DIPEA (1.378 ml, 7.909 mmol) in CH3CN (15 ml) was heated in a sealed tube at 100° C. for 5 days. After cooling, the solvent was concentrated in vacuo. The residue was purified by column chromatography (silica gel; Heptane/EtOAc 100/10 to 80/20 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D55 (0.56 g, 42%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel; Heptane/EtOAc 100/10 to 80/20 as eluent)
  4. customThe desired fractions were collected
  5. concentrationconcentrated in vacuo
  6. customto yield intermediate D55 (0.56 g, 42%)

Sources & evidence

ORD record
ord-e4239f840bdb48a38cc4f6e2bf399aa1
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

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