1-Phenylpiperazine → HCID 10132780, compound

HRID 2086393Notes

Reaction equation

HRID 2086393 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH:13]=O)[O:8][N:7]=1.[C:15]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:15]1([N:21]2[CH2:26][CH2:25][N:24]([CH2:13][CH2:12][CH2:11][C:9]3[O:8][N:7]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727325HCID 22727325, compound

Product 1

HCID 10132780HCID 10132780, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(2-thienyl)isoxazol-5-yl]propanal (20 mg, 0.1 mmol), 1-phenylpiperazine (14.7, 0.1 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (61.4 mg, 0.3 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 3.5 hr and followed the same processes as in Example 1 to obtain 26.4 mg (77.4%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 3.5 hr

Sources & evidence

ORD record
ord-6b81922bdf3248fabfb0d64324b860e7
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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