1-(2,4-Xylyl)piperazine → 1-(3-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-4-(2,4-dimethylphenyl)piperazine

HRID 387082Notes

Reaction equation

HRID 387082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:19][CH2:20][CH:21]=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:19][CH2:20][CH2:21][N:34]3[CH2:35][CH2:36][N:31]([C:25]4[CH:26]=[CH:27][C:28]([CH3:30])=[CH:29][C:24]=4[CH3:23])[CH2:32][CH2:33]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 705441-(2,4-Xylyl)piperazineHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866399243-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal

Product 1

HCID 250642251-(3-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-4-(2,4-dimethylphenyl)piperazine

Procedure

96 mg (70%) of target compound was obtained by using a method same as in Example 1 by using 3-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal (80 mg, 0.272 mmol), 1-(2,4-dimethylphenyl)piperazine (52 mg, 0.272 mmol), DIPEA (0.071 mL, 0.408 mmol) and NaBH(OAc)3 (173 mg, 0.816 mmol).

Workup

  1. custom96 mg (70%) of target compound was obtained

Sources & evidence

ORD record
ord-6e947b55261f4df0892debe68ef385a5
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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