Acetic Acid → 4-(2-{4-[2-(1-Oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519650Notes

Reaction equation

HRID 1519650 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]3[C:13](=[O:16])[O:14][CH2:15][C:11]=3[CH:10]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.O=[CH:20][CH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.C([BH3-])#N.[Na+].CC(O)=O>CO>[O:16]=[C:13]1[C:12]2[CH:17]=[CH:18][C:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][N:4]([CH2:20][CH2:21][C:22]4[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=4)[CH2:3][CH2:2]3)=[CH:10][C:11]=2[CH2:15][O:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 125916704-(2-Oxoethyl)benzonitrileHCID 595686715-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one

Product 1

HCID 569708614-(2-{4-[2-(1-Oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one (50 mg, 0.20 mmol), 4-(2-Oxoethyl)benzonitrile (30 mg, 0.20 mmol), Sodium Cyanoborohydride (13 mg, 0.20 mmol), and a drop of HOAc was stirred together in Methanol for 2 hours. LC showed formation of the desired product. The crude was diluted with EtOAc, washed with water, adsorbed onto silica gel, and purified by silica gel chromatography. LC-MS (IE, m/z): 376 [M+1]+. (0.30 μM)

Sources & evidence

ORD record
ord-bba5943f108d44419a1f1aec794c747b
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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