Diisopropylethylamine → 4-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-2-methyl-1-m-tolylpiperazine

HRID 387047Notes

Reaction equation

HRID 387047 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][CH:25]1[CH2:30][NH:29][CH2:28][CH2:27][N:26]1[C:31]1[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=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:4]=[CH:5][C:6]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:12]=[C:11]([CH2:20][CH2:21][CH2:22][N:29]3[CH2:28][CH2:27][N:26]([C:31]4[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=4)[CH:25]([CH3:24])[CH2:30]3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 27238042-Methyl-1-(m-tolyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399203-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250665054-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-2-methyl-1-m-tolylpiperazine

Procedure

120 mg (89%) 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 (80 mg, 0.261 mmol), 2-methyl-1-m-tolylpiperazine (50 mg, 0.261 mmol), DIPEA (0.068 mL, 0.392 mmol) and NaBH(OAc)3 (166 mg, 0.783 mmol).

Workup

  1. custom120 mg (89%) of target compound was obtained

Sources & evidence

ORD record
ord-12e048675cb3402ea538ee4793c399a0
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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