Sodium borohydride → HCID 58779106, compound

HRID 1371903Notes

Reaction equation

HRID 1371903 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:14][CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)([O-])=O.[BH4-].[Na+]>CO>[NH2:2][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:14][CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21071643HCID 21071643, compound

Product 1

HCID 58779106HCID 58779106, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine N-(2-(5-nitro-1H-indol-3-yl)ethyl)-3-phenoxybenzylamine hydrochloride (250 mg, 0.64 mmol) and NiCl2-6H2O (460 mg, 1.9 mmol) in 30 mL MeOH and treat with NaBH4 (73 mg, 1.9 mmol). After 1 hour concentrate to dryness, partition between EtOAc and concentrated NH4OH. Extract the aqueous layer with EtOAc, combine the organic layer, dry over MgSO4 and concentrate to dryness. Chromatograph on silica gel eluting with a stepwise gradient 20/75/5 THF/hexanes/Et3N then 40/55/5 THF/hexanes/Et3N gives the title compound as an oil. Additional chromatograph on silica gel eluting with 1% MeOH in CHCl3 mixed with conc. NH4OH gives the title compound as an oil. Treatment with in 10 mL EtOH with 0.25 mL 5N HCl and 40 mL toluene then concentrating give the title compound as the hydrochloride: Analysis for C23H23N3O 2.6 HCl 0.6 EtOH: calcd: C, 59.66; H, 5.83; N, 9.07; found: C, 59.30; H, 5.48; N, 8.82; ISMS 358 (M+1).

Workup

  1. concentrationAfter 1 hour concentrate to dryness
  2. custompartition between EtOAc and concentrated NH4OH
  3. extractionExtract the aqueous layer with EtOAc
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-19389159bcbe4a93ad4c0700b05cb490
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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