Methanol → HCID 59441878, compound

HRID 1014349Notes

Reaction equation

HRID 1014349 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.CO.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59441746HCID 59441746, compound

Product 1

HCID 59441878HCID 59441878, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[3-(methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)hexahydro-1H-1,4-diazepine (0.737g, 2.24 mmol) was suspended in 5 mL THF and 10 mL MeOH in a 100 mL round bottom flask. NiCl2-6H2O (159 mg, 0.672 mmol) was added followed by slow addition of NaBH4 (254 mg, 6.72 mmol). Reaction mixture was adsorbed onto SiO2 and purified via column chromatography to afford 2-(methyloxy)-4-[4-(methylsulfonyl)hexahydro-1H-1,4-diazepin-1-yl]aniline (340 mg, 51%) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.82-1.94 (m, 2 H) 2.80 (s, 3 H) 3.17 (t, J=5.82 Hz, 2 H) 3.36-3.43 (m, 2 H) 3.49 (dd, J=10.68, 3.99 Hz, 4 H) 3.75 (br. s., 3 H) 4.01-4.15 (m, 2 H) 6.10-6.20 (m, 1 H) 6.26-6.35 (m, 1 H) 6.48-6.59 (m, 1 H). ESIMS (M+H)+301

Workup

  1. customReaction mixture
  2. custompurified via column chromatography

Sources & evidence

ORD record
ord-9190e9541440433f893a4fe268879a37
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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