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

HRID 387144Notes

Reaction equation

HRID 387144 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.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH2:14][CH2:13][CH2:12][C:11]3[N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=[C:9]([CH2:16][CH2:17][CH3:18])[CH:10]=3)[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 974781-(4-Chlorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399323-(1-phenyl-3-propyl-1H-pyrazol-5-yl)propanal

Product 1

HCID 685589731-(4-chlorophenyl)-4-(3-(1-phenyl-3-propyl-1H-pyrazol-5-yl)propyl)piperazine

Procedure

118 mg (83%) 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 (75 mg, 0.310 mmol), 1-(4-chlorophenyl)piperazine (83 mg, 0.310 mmol), DIPEA (0.081 mL, 0.465 mmol) and NaBH(OAc)3 (197 mg, 0.930 mmol).

Workup

  1. custom118 mg (83%) of target compound was obtained

Sources & evidence

ORD record
ord-f5cf3778bcd748a29577da9bf1a12f7b
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

Loading…