1-Benzylpiperazine → 457660-81-0

HRID 2086442Notes

Reaction equation

HRID 2086442 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].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33]C[CH2:31][CH2:30]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:49]([N:56]1CCNCC1)C1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:49][N:56]3[CH2:33][CH2:34][N:29]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][CH3:21])[CH2:30][CH2:31]3)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 759941-BenzylpiperazineHCID 2319651-(2-methoxyphenyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 22727348HCID 22727348, compound

Product 1

HCID 11633816457660-81-0Yield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3,4-dimethoxyphenyl)isoxazol-5-yl]butanal (33.2 mg, 0.121 mmol) and 1-(2-methoxyphenyl)piperidine (23.3 mg, 0.121 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (76.9 mg, 0.363 mmol), cold acetic acid (8.3, 0.145 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 3 hr and followed the same processes as in Example 1 to obtain 33.2 mg (60.8%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 3 hr

Sources & evidence

ORD record
ord-496924b8ec2f4d27bd89fc7c255f5b9c
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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