Acetic Acid → HCID 10156694, compound

HRID 2086437Notes

Reaction equation

HRID 2086437 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:10]=[C:9]([CH:11](C)[CH2:12][CH:13]=O)[O:8][N:7]=1.[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:31](C)=O.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([CH2:31][CH2:13][CH2:12][CH2:11][C:9]2[O:8][N:7]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 759941-BenzylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22727329HCID 22727329, compound

Product 1

HCID 10156694HCID 10156694, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-(3-(2-thienyl)isoxazol-5-yl)butanal (21 mg, 0.095 mmol) and 1-benzylpiperazine (16.5, 0.095 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (60.4 mg, 0.285 mmol), cold acetic acid (6.5, 0.114 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 4.2 hr and followed the same processes as in Example 1 to obtain 13.9 mg (81.0%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 4.2 hr

Sources & evidence

ORD record
ord-c2bf9a5c7ccf473eadc7eb26bc2a6bfe
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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