Acetic Acid → HCID 21963415, compound

HRID 2211879Notes

Reaction equation

HRID 2211879 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH2:24])[CH2:12][CH2:11]2)=[N:2]1.[CH3:25][C:26]([CH3:28])=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)CCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][CH:26]([CH3:28])[CH3:25])[CH2:12][CH2:11]2)=[N:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 21963169HCID 21963169, compound

Product 1

HCID 21963415HCID 21963415, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A round bottomed flask was charged with 4.9 g (0.015 mol) 2-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine, 50 mL ClCH2CH2Cl, 1.2 mL (0.016 mol) acetone, 0.93 mL (0.016 mol) HOAc, and 5.2 g (0.024 mol) NaBH(OAc)3. After stirring for 15 h at rt the reaction was quenched with 50 mL 2M K2CO3. The organic layer was separated, dried and concentrated in vacuo to give 5.5 g (100% yield) of the desired material as a yellow-orange oil. MS (APCI): 381 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J=8 Hz, 1H), 7.70 (d, J=8 Hz, 1H), 7.47–7.42 (m, 1H), 7.35–7.31 (m, 1H), 7.03–7.00 (m, 2H), 6.54–6.50 (m, 2H), 3.61–3.55 (m, 5H), 2.75–2.71 (m, 6H), 2.65–2.60 (m, 2H), 1.18 (d, J=6 Hz, 6H).

Workup

  1. customwas quenched with 50 mL 2M K2CO3
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-744d131ba7714aebb41792cff844f508
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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