Diisopropylethylamine → 1-(4-chlorophenyl)-4-(3-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)piperazine

HRID 883352Notes

Reaction equation

HRID 883352 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.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH2:35][CH2:34][N:33]([CH2:21][CH2:20][CH2:19][C:10]3[CH:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[N:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:11]=3)[CH2:32][CH2:31]2)=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 974781-(4-Chlorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399243-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal

Product 1

HCID 250642241-(4-chlorophenyl)-4-(3-(5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

100 mg (72%) 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-(4-chlorophenyl)piperazine (73 mg, 0.272 mmol), DIPEA (0.071 mL, 0.408 mmol) and NaBH(OAc)3 (173 mg, 0.816 mmol).

Workup

  1. custom100 mg (72%) of target compound was obtained

Sources & evidence

ORD record
ord-bae766e3a0ef4b3cb0cab8f427bea46c
Source dataset
uspto-grants-2012_08
Patent number
US08236806B2

Reaction notes

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