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

HRID 387022

Reaction equation

[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:19][CH2:20][CH:21]=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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:9]3[CH:10]=[C:11]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[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:28][CH:29]=1

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 974781-(4-Chlorophenyl)piperazine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399183-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250656581-(4-chlorophenyl)-4-(3-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

73 mg (52%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)propanal (80 mg, 0.276 mmol), 1-(4-chlorophenyl)piperazine (74 mg, 0.276 mmol), DIPEA (0.072 mL, 0.414 mmol) and NaBH(OAc)3 (175 mg, 0.828 mmol).

Workup

custom73 mg (52%) of target compound was obtained

Sources & evidence

ORD record: ord-1b080a4f47b44019b45ec5501ba93b1d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Linked notes

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