Benzhydrylpiperazine → HCID 10299607, compound

HRID 2086400Notes

Reaction equation

HRID 2086400 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH:17]=O)[O:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:19]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:32]1([CH:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]2[CH2:27][CH2:28][N:29]([CH2:17][CH2:16][CH2:15][C:13]3[O:12][N:11]=[C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[CH:14]=3)[CH2:30][CH2:31]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 70048BenzhydrylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727321HCID 22727321, compound

Product 1

HCID 10299607HCID 10299607, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3-nitrophenyl)isoxazol-5-yl]propanal (10 mg, 0.04 mmol) and 1-(diphenylmethyl)piperazine (10 mg, 0.04 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (26 mg, 0.12 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 18.2 hr and followed the same processes as in Example 1 to obtain 17.6 mg (89.8%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 18.2 hr

Sources & evidence

ORD record
ord-02d9c243f1e54433ace5e695e7daa19b
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

Loading…