1-(2-Methoxyphenyl)piperazine → 2-methoxy-1-{4-[3-(3-phenylisoxazol-5-yl)propyl]piperazinyl}Benzene

HRID 2086403Notes

Reaction equation

HRID 2086403 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][CH2:13][CH:14]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:27]([CH2:14][CH2:13][CH2:12][C:10]2[O:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 14816484HCID 14816484, compound

Product 1

HCID 101342092-methoxy-1-{4-[3-(3-phenylisoxazol-5-yl)propyl]piperazinyl}BenzeneYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-(3-phenylisoxazol-5-yl)propanal (10 mg, 0.05 mmol) and 1-(2-methoxyphenyl)piperazine (19.2 mg, 0.10 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (32 mg, 0.15 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 16.5 hr and followed the same processes as in Example 1 to obtain 10 mg (53.0%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 16.5 hr

Sources & evidence

ORD record
ord-864e93a141174db18377eb41a202bd49
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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