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

HRID 387147

Reaction equation

[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH:14]=O)=[CH:10][C:9]([CH2:16][CH2:17][CH3:18])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:28][CH2:29][N:30]([CH2:14][CH2:13][CH2:12][C:11]2[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=[C:9]([CH2:16][CH2:17][CH3:18])[CH:10]=2)[CH2:31][CH2:32]1

Participants

Reactant 4

HCID 705411-(2,3-Xylyl)piperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 86639932HCID 86639932, compound

Product 1

HCID 685542451-(2,3-dimethylphenyl)-4-(3-(1-phenyl-3-propyl-1H-pyrazol-5-yl)propyl)piperazine

Procedure

146 mg (78%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-phenyl-3-propyl-1H-pyrazol-5-yl)propanal (100 mg, 0.413 mmol), 1-(2,3-dimethylphenyl)piperazine (79 mg, 0.413 mmol), DIPEA (0.110 mL, 0.620 mmol) and NaBH(OAc)3 (263 mg, 1.239 mmol).

Workup

custom146 mg (78%) of target compound was obtained

Sources & evidence

ORD record: ord-7c739a4b97d84f3bba2f051cfcfd6502
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Linked notes

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