1-Benzylpiperazine → HCID 10296694, compound

HRID 2086435Notes

Reaction equation

HRID 2086435 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:15]=[C:14]([CH:16](C)[CH2:17][CH:18]=O)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:36](C)=O.[Na+].FC(F)(F)C1C=CC=CC=1CN1CCNCC1>C(Cl)Cl>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:36][N:31]3[CH2:32][CH2:33][N:28]([CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:29][CH2:30]3)[O:13][N:12]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 759941-BenzylpiperazineHCID 30233221-((2-(Trifluoromethyl)phenyl)methyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727348HCID 22727348, compound

Product 1

HCID 10296694HCID 10296694, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3,4-dimethoxyphenyl)isoxazol-5-yl]butanal (32 mg, 0.116 mmol) and 1-benzylpiperazine (20, 0.116 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (73.8 mg, 0.348 mmol), cold acetic acid (8.0, 0.139 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 4.5 hr and followed the same processes as in Example 1 to obtain 35.7 mg (70.7%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 4.5 hr

Sources & evidence

ORD record
ord-1205ca4e52514dc68f4605fe016f89bb
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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