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

HRID 387080Notes

Reaction equation

HRID 387080 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.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][N:33]([CH2:21][CH2:20][CH2:19][C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=2)[CH2:32][CH2:31]1

Participants

5

Reactant 4

HCID 705291-(2-Fluorophenyl)piperazineHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866399243-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal

Product 1

HCID 250642231-(2-fluorophenyl)-4-(3-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

57 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 (55 mg, 0.187 mmol), 1-(2-fluorophenyl)piperazine (0.027 mL, 0.170 mmol), DIPEA (0.030 mL, 0.170 mmol) and NaBH(OAc)3 (108 mg, 0.510 mmol).

Workup

  1. custom57 mg (70%) of target compound was obtained

Sources & evidence

ORD record
ord-e90cfb7c05214f94a45a300f8cbf0032
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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