Diisopropylethylamine → 1-(4-chlorophenyl)-4-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)piperazine

HRID 387042Notes

Reaction equation

HRID 387042 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.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH2:36][CH2:35][N:34]([CH2:22][CH2:21][CH2:20][C:11]3[CH:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:13]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:12]=3)[CH2:33][CH2:32]2)=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 974781-(4-Chlorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399203-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250663071-(4-chlorophenyl)-4-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

112 mg (82%) 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), 1-(4-chlorophenyl)piperazine (70 mg, 0.261 mmol), DIPEA (0.068 mL, 0.392 mmol) and NaBH(OAc)3 (166 mg, 0.783 mmol).

Workup

  1. custom112 mg (82%) of target compound was obtained

Sources & evidence

ORD record
ord-414430ac866945418cf29957b017062f
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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