Diisopropylethylamine → 1-(3,4-dichlorophenyl)-4-(3-(1,5-diphenyl-1H-pyrazol-3-yl)propyl)piperazine

HRID 387008Notes

Reaction equation

HRID 387008 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:18][CH2:19][CH:20]=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:26]=[CH:27][C:28]=1[Cl:29].CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[Cl:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:35][CH2:34][N:33]([CH2:20][CH2:19][CH2:18][C:9]3[CH:10]=[C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH2:32][CH2:31]2)[CH:26]=[CH:27][C:28]=1[Cl:29]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 426311353-(1,5-diphenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250652581-(3,4-dichlorophenyl)-4-(3-(1,5-diphenyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

110 mg (72%) of target compound was obtained by using a method same as in Example 1 by using 3-(1,5-diphenyl-1H-pyrazol-3-yl)propanal (80 mg, 0.289 mmol), 1-(3,4-dichlorophenyl)piperazine (67 mg, 0.289 mmol), DIPEA (0.076 mL, 0.434 mmol) and NaBH(OAc)3 (184 mg, 0.868 mmol).

Workup

  1. custom110 mg (72%) of target compound was obtained

Sources & evidence

ORD record
ord-c517b7ad04e445b29cfc09f32ca09524
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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