Sodium borohydride → HCID 46199223, compound

HRID 1966471Notes

Reaction equation

HRID 1966471 reaction equation
[CH2:1]([N:8]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[CH:12]=[CH:11][C:10]=1[N+:29]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([N:8]([C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:28])[CH2:17][CH2:16]2)[CH:12]=[CH:11][C:10]=1[NH2:29])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 46198774HCID 46198774, compound

Product 1

HCID 46199223HCID 46199223, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

A suspension of N-benzyl-5-(4-benzoylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (1.2 g, 2.4 mmol), 2 M copper sulfate solution (10 ml, 2.0 mmol), and sodium borohydride (0.46 g, 12.2 mmol) in 40 ml ethanol was stirred at room temperature overnight. The run was quenched with additional 20 ml water, and it was extracted with acetyl acetate (3×20 ml). (4-(3-(N-benzyl-N-phenylamino)-4-aminophenyl)piperazin-1-yl)(phenyl)methanone (0.8 g, 71%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.29 (d, br, 4H), 3.56 (s, br, 4H), 3.93 (s, 2H), 4.88 (s, 2H), 6.68 (d, J=7.9 Hz, 2H), 6.80 (m, 4H), 7.19 (dd, J=7.4, 8.7 Hz, 2H), 7.25-7.45 (m, 5H), 7.47 (s, 5H). 13C NMR (125 MHz, CDCl3): δ (ppm) 51.6, 51.8, 51.9, 56.1, 114.2, 117.8, 118.1, 118.4, 119.5, 127.4, 127.5, 127.6, 128.9, 129.0, 129.7, 130.0, 133.9, 136.2, 138.8, 139.5, 145.1, 148.2, 170.8.

Workup

  1. customThe run was quenched with additional 20 ml water, and it
  2. extractionwas extracted with acetyl acetate (3×20 ml)

Sources & evidence

ORD record
ord-c1f0510b7fdc41b3b81a9e32d8865265
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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