1-Benzylpiperazine → HCID 22727323, compound

HRID 2086441Notes

Reaction equation

HRID 2086441 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:14]=[C:13]([CH:15](C)[CH2:16][CH:17]=O)[O:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32]C[CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:48]([N:55]1CCNCC1)C1C=CC=CC=1>C(Cl)Cl>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][N:55]([CH2:48][CH2:17][CH2:16][CH2:15][C:13]2[O:12][N:11]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH:14]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 759941-BenzylpiperazineHCID 2319651-(2-methoxyphenyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 22727367HCID 22727367, compound

Product 1

HCID 22727323HCID 22727323, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3-nitrophenyl)isoxazol-5-yl]butanal (60 mg, 0.231 mmol) and 1-(2-methoxyphenyl)piperidine (44.4 mg, 0.231 mmol) in 3 mL of dry methylene chloride, were added NaBH(OAc)3 (147 mg, 0.693 mmol), cold acetic acid (15.9, 0.277 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 4.2 hr and followed the same processes as in Example 1 to obtain 80.8 mg (80.1%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 4.2 hr

Sources & evidence

ORD record
ord-146cff18ec5a48709e2026aa14594778
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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