1-Phenylpiperazine → HCID 10271912, compound

HRID 2086439Notes

Reaction equation

HRID 2086439 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13](C)[CH2:14][CH:15]=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:18]([N:25]1[CH2:30][CH2:29]C[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:45]1([N:51]2CCNCC2)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:45][N:51]3[CH2:29][CH2:30][N:25]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 761901-BenzylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 22727344HCID 22727344, compound

Product 1

HCID 10271912HCID 10271912, compoundYield 120.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(4-fluorophenyl)isoxazol-5-yl]butanal (25 mg, 0.104 mmol) and 1-benzylpiperidine (37.2, 0.214 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (136 mg, 0.642 mmol), cold acetic acid (14.7, 0.257 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 1.5 hr and followed the same processes as in Example 1 to obtain 49.2 mg (58.4%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 1.5 hr

Sources & evidence

ORD record
ord-96f5cd42f19a42caa20cbf46ff8da5a5
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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