1-(2,3-Xylyl)piperazine → 1-(2,3-dimethylphenyl)-4-(3-(1,5-diphenyl-1H-pyrazol-3-yl)propyl)piperazine

HRID 387005

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.[CH3:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[N:30]1[CH2:31][CH2:32][N:33]([CH2:20][CH2:19][CH2:18][C:9]2[CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:34][CH2:35]1

Participants

Reactant 4

HCID 705411-(2,3-Xylyl)piperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 426311353-(1,5-diphenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250650491-(2,3-dimethylphenyl)-4-(3-(1,5-diphenyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

77 mg (81%) 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 (64 mg, 0.231 mmol), 1-(2,3-dimethylphenyl)piperazine (40 mg, 0.210 mmol), DIPEA (0.037 mL, 0.210 mmol) and NaBH(OAc)3 (156 mg, 0.735 mmol).

Workup

custom77 mg (81%) of target compound was obtained

Sources & evidence

ORD record: ord-b5673ea7824540dc901c271c560f168a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Linked notes

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