Water → HCID 59808274, compound

HRID 563147Notes

Reaction equation

HRID 563147 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:12][C@@H:13]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)=[O:15].[BH4-].[Na+].O>CO>[CH2:22]([N:19]1[CH2:18][CH2:17][N:16]([C:14](=[O:15])[C@@H:13]([NH:12][CH2:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:21][CH2:20]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 589040Indole-5-carboxaldehydeHCID 4311764Sodium borohydrideHCID 10687394HCID 10687394, compound

Product 1

HCID 59808274HCID 59808274, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an inert atmosphere, indole-5-carboxaldehyde (108 mg, 0.75 mmol) and 2-amino-1-(4-benzyl-piperazin-1-yl)-(S)-3-phenyl-propan-1-one (162 mg, 0.50 mmol) were dissolved in dry MeOH (4.0 mL) and refluxed for 4 h. The reaction mixture was cooled to rt followed by slow addition of sodium borohydride (28 mg, 0.75 mmol). Stirring was continued for 1 h. Water (1 mL) was added to the reaction mixture followed by evaporation of the solvent under reduced pressure. The residue was dissolved in EtOAc (10 mL) and washed with sat. sodium hydrogencarbonate solution (10 mL) and brine (10 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give 200 mg (80%) of 1-(4-benzyl-piperazin-1-yl)-2-[(1H-indol-5-ylmethyl)-amino]-(S)-3-phenyl-propan-1-one. LC-MS: tR=0.65 min; [M+H]+=453.39.

Workup

  1. temperaturerefluxed for 4 h
  2. customfollowed by evaporation of the solvent under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (10 mL)
  4. washwashed with sat. sodium hydrogencarbonate solution (10 mL) and brine (10 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fc73d96caff41a3b6fcc150f0cfb168
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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