Acetic Acid → HCID 10226938, compound

HRID 2086438Notes

Reaction equation

HRID 2086438 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]2[CH:18]=[C:17]([CH:19](C)[CH2:20][CH:21]=O)[O:16][N:15]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:39](C)=O.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:24]([N:31]1[CH2:36][CH2:35][N:34]([CH2:39][CH2:21][CH2:20][CH2:19][C:17]2[O:16][N:15]=[C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=3)[CH:18]=2)[CH2:33][CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 759941-BenzylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727366HCID 22727366, compound

Product 1

HCID 10226938HCID 10226938, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3-phenoxyphenyl)isoxazol-5-yl]butanal (31 mg, 0.101 mmol) and 1-benzylpiperazine (17.6, 0.101 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (64.2 mg, 0.303 mmol), cold acetic acid (6.9, 0.121 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 17 hr and followed the same processes as in Example 1 to obtain 20.1 mg (42.6%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 17 hr

Sources & evidence

ORD record
ord-188a7ba9db6541b1a2d2af38419232c2
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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