1-(2,3-Xylyl)piperazine → HCID 25066503, compound

HRID 883326Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:20][CH2:21][CH:22]=O)[CH:10]=2)=[CH:5][CH:4]=1.[CH3:24][C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:20][CH2:21][CH2:22][N:35]3[CH2:36][CH2:37][N:32]([C:26]4[CH:27]=[CH:28][CH:29]=[C:30]([CH3:31])[C:25]=4[CH3:24])[CH2:33][CH2:34]3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 705411-(2,3-Xylyl)piperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399203-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 25066503HCID 25066503, compound

Procedure

117 mg (93%) of target compound was obtained by using a method same as in Example 1 by using 3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal (75 mg, 0.245 mmol), 1-(2,3-dimethylphenyl)piperazine (47 mg, 0.245 mmol), DIPEA (0.064 mL, 0.368 mmol) and NaBH(OAc)3 (156 mg, 0.735 mmol).

Workup

custom117 mg (93%) of target compound was obtained

Sources & evidence

ORD record: ord-bf802e212d644aebb0b0535594bc3d7a
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236806B2

Reaction notes

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