Triethylamine → 5-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)-2-benzofuran-1(3H)-one

HRID 1519646Notes

Reaction equation

HRID 1519646 reaction equation
O=[O+][O-].[CH2:4]([C:7]1[CH:16]=[CH:15][C:10]2[C:11](=[O:14])[O:12][CH2:13][C:9]=2[CH:8]=1)[CH:5]=C.Cl.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:23][CH:22]=1)([O-:20])=[O:19].C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][N:32]([CH2:5][CH2:4][C:7]3[CH:16]=[CH:15][C:10]4[C:11](=[O:14])[O:12][CH2:13][C:9]=4[CH:8]=3)[CH2:33][CH2:34]2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 24823OzoneHCID 5049666Sodium triacetoxyborohydrideHCID 666439845-allyl-2-benzofuran-1(3H)-oneHCID 666440061-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride

Product 1

HCID 675174115-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ozone was bubbled through a solution of 5-allyl-2-benzofuran-1(3H)-one (125 mg, 0.72 mmol) in DCM until the color changed to orange. Removed excess ozone by bubbling nitrogen through solution for a minute. Added a solution of 1-[2-(4-nitrophenyl)ethyl]piperazine hydrochloride (65 mg, 0.24 mmol) and triethylamine (0.033 mL, 0.24 mmol) in DCM (2 mL), followed by NaB(OAc)3H (250 mg, 1.2 mmol). The mixture was allowed to stir at RT for 16 hours. HPLC-MS shows product but reaction is not clean. The product was urified by prep-TLC to afford 5-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)-2-benzofuran-1(3H)-one as a white solid. LC-MS (IE, m/z): 396 [M+1]+. (0.089 μM)

Workup

  1. customRemoved excess ozone by bubbling nitrogen through solution for a minute
  2. customproduct but reaction

Sources & evidence

ORD record
ord-4b9841f6c47a4788bcf5da7a9c0d69fb
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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