1-(2-Fluorophenyl)piperazine → 1-(2-fluorophenyl)-4-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)piperazine

HRID 387041Notes

Reaction equation

HRID 387041 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:20][CH2:21][CH:22]=O)[CH:10]=2)=[CH:5][CH:4]=1.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=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:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][N:34]([CH2:22][CH2:21][CH2:20][C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:12]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 4

HCID 705291-(2-Fluorophenyl)piperazineHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866399203-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250663061-(2-fluorophenyl)-4-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

65 mg (53%) of target compound was obtained by using a method same as in Example 1 by using 3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal (75 mg, 0.245 mmol), 1-(2-fluorophenyl)piperazine (44 mg, 0.245 mmol), DIPEA (0.064 mL, 0.368 mmol) and NaBH(OAc)3 (156 mg, 0.735 mmol).

Workup

  1. custom65 mg (53%) of target compound was obtained

Sources & evidence

ORD record
ord-17768f68f4874d938f62d6608eccf47d
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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