1-Phenylpiperazine → HCID 69890254, compound

HRID 2086394Notes

Reaction equation

HRID 2086394 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:13]=[C:12]([CH2:14][CH2:15][CH:16]=O)[O:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:18]1([N:24]2[CH2:29][CH2:28][N:27]([CH2:16][CH2:15][CH2:14][C:12]3[O:11][N:10]=[C:9]([CH:8]=[CH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:13]=3)[CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 73993903HCID 73993903, compound

Product 1

HCID 69890254HCID 69890254, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(2-phenylvinyl)isoxazol-5-yl]propanal (20 mg, 0.09 mmol) and 1-phenylpiperazine (13.4, 0.09 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (56 mg, 0.26 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 22 hr and followed the same processes as in Example 1 to obtain 16.2 mg (49.3%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 22 hr

Sources & evidence

ORD record
ord-22d8c27594fa4d1289f9d5f57cfe681b
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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