1-Phenylpiperazine → 1-(3-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

HRID 387060

Reaction equation

[Cl: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.[C:23]1([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[Cl: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][CH2:21][N:32]3[CH2:33][CH2:34][N:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:30][CH2:31]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 70961-Phenylpiperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399223-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal

Product 1

HCID 250669121-(3-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

Procedure

121 mg (80%) of target compound was obtained by using a method same as in Example 1 by using 3-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-propanal (100 mg, 0.307 mmol), 1-phenylpiperazine (0.046 mL, 0.307 mmol), DIPEA (0.080 mL, 0.461 mmol) and NaBH(OAc)3 (195 mg, 0.921 mmol).

Workup

custom121 mg (80%) of target compound was obtained

Sources & evidence

ORD record: ord-9974c0eda9a94780a634ec65efd73fca
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Linked notes

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