Water → HCID 57894430, compound

HRID 1677832Notes

Reaction equation

HRID 1677832 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:18]([N:22]1C(=O)C2C(=CC=CC=2)C1=O)[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.O>CCO>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:18]([NH2:22])[CH:19]([CH3:20])[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 57894445HCID 57894445, compound

Product 1

HCID 57894430HCID 57894430, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of product of step 7 (0.4 mmol) in 10 mL of EtOH, was added hydrazine (4 mmol) at 0° C. The mixture was stirred at 80° C. overnight. The solution was poured into water, and extracted with EtOAc (×3). The organic layers were combined, washed with 10% NaOH, H2O (×3), brine (×3), dried (Na2SO4), filtered, and the filtrate was concentrated. The material was purified by flash chromatography (20% EtOAc:hexane) to yield 52 mg of 1-(1-benzyl-5-chloro-1H-indole-2-yl)-2-methylpropan-1-amine.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with 10% NaOH, H2O (×3), brine (×3)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe material was purified by flash chromatography (20% EtOAc:hexane)

Sources & evidence

ORD record
ord-8a31b4e1d5154ce2851095022398e0e1
Source dataset
uspto-grants-2011_08
Patent number
US08008335B2

Reaction notes

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