1-(2-Methoxyphenyl)piperazine → HCID 10181568, compound

HRID 2086411Notes

Reaction equation

HRID 2086411 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:15]=[C:14]([CH2:16][CH2:17][CH:18]=O)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[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][NH:31][CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>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][N:31]3[CH2:30][CH2:29][N:28]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:21][CH3:20])[CH2:33][CH2:32]3)[O:13][N:12]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727343HCID 22727343, compound

Product 1

HCID 10181568HCID 10181568, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3,4-dimethoxyphenyl)isoxazol-5-yl]propanal (10 mg, 0.04 mmol) and 1-(2-methoxyphenyl)piperazine (7.4 mg, 0.04 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (24 mg, 0.12 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 22.6 hr and followed the same processes as in Example 1 to obtain 18.9 mg (100%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 22.6 hr

Sources & evidence

ORD record
ord-6bfe76133ac1431b8597dad23a8ad1c8
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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