1-Phenylpiperazine → 1-(3-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

HRID 387030Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:18][CH2:19][CH:20]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:22]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:18][CH2:19][CH2:20][N:31]2[CH2:32][CH2:33][N:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:29][CH2:30]2)=[N:6]1)([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 4

HCID 70961-Phenylpiperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399193-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-3-yl)propanal

Product 1

HCID 250658741-(3-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

Procedure

125 mg (90%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-3-yl)propanal (85 mg, 0.297 mmol), 1-phenylpiperazine (0.045 mL, 0.297 mmol), DIPEA (0.078 mL, 0.446 mmol) and NaBH(OAc)3 (189 mg, 0.891 mmol).

Workup

custom125 mg (90%) of target compound was obtained

Sources & evidence

ORD record: ord-4e939fd1f48c4382804297a50ac7af20
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Reaction notes

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