Sodium triacetoxyborohydride → 2-Methoxy-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519575Notes

Reaction equation

HRID 1519575 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH:12]=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=1)([O-:16])=[O:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.CC(O)=O>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][N:28]2[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][C:20]3[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=3)[CH2:26][CH2:27]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazineHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Product 1

HCID 675141312-Methoxy-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methoxy-4-(2-oxoethyl)benzonitrile (100 mg, 0.57 mmol), 1-[2-(4-Nitrophenyl)ethyl]piperazine (134 mg, 0.51 mmol) in 60 mL of dry methanol were added 2 drop of HOAc and then stirred at room temperature for 1 hr. Then NaBH(OAc)3 (362 mg, 1.71 mmol) was added an the then the mixture was stirred overnight. Concentrated and the residue was purified via prep-TLC to give 2-methoxy-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile. 1H-NMR (300 MHz, CDCl3) δ ppm 8.14 (d, J=8.6 Hz, 2H), 7.35˜7.47 (m, 3H), 6.79˜6.85 (m, 2H), 3.12 (s, 3H), 2.48˜2.96 (m, 16H). MS m/z: 395 (M+1)+. (0.052 μM)

Workup

  1. stirringwas stirred overnight
  2. concentrationConcentrated
  3. customthe residue was purified via prep-TLC

Sources & evidence

ORD record
ord-231549bf100649a29b2ea7fd706f9df6
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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