Ethanol → HCID 86645783, compound

HRID 1042968Notes

Reaction equation

HRID 1042968 reaction equation
Cl.[CH2:2]([NH:6][CH2:7][CH2:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)=[O:10])[CH:3]([CH3:5])[CH3:4].C(O)C.[OH-].[Na+].[Na]>CC(C)=O>[CH2:2]([NH:6][CH2:7][CH2:8][CH:9]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[OH:10])[CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 66870322HCID 66870322, compound

Product 1

HCID 86645783HCID 86645783, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-(isobutylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (4.2 g, 19.4 mmol) and ethanol (10 mL) at 4° C. sodium hydroxide (1.6 g of a 50% aqueous solution) was added in about 20 minutes. Afterwards, neat sodium borhydride (0.37 g, 9.7 mmol, 1.0 eq) was added in several portions in about 30 minutes. At the end of the addition, the suspension was stirred for 4 h at the same temperature, then acetone (10.0 mL) was added dropwise in 20 minutes and the mixture was stirred for 10 additional minutes. Afterwards the precipitate was removed by filtration and the mixture was concentrated under vacuum affording an orange oil. The crude product was purified by column chromatography using a 40:10:1 (v:v:v) mixture of methylene chloride/methanol/ammonium hydroxide (25% aqueous solution) affording 3.1 g (76% yield) of product.

Workup

  1. additionwas added in about 20 minutes
  2. additionAt the end of the addition
  3. stirringthe mixture was stirred for 10 additional minutes
  4. customAfterwards the precipitate was removed by filtration
  5. concentrationthe mixture was concentrated under vacuum
  6. customaffording an orange oil
  7. customThe crude product was purified by column chromatography
  8. additiona 40:10:1 (v:v:v) mixture of methylene chloride/methanol/ammonium hydroxide (25% aqueous solution)

Sources & evidence

ORD record
ord-54512c9ddcfb4c79ba8e783f2db8ff72
Source dataset
uspto-grants-2013_10
Patent number
US08558014B2

Reaction notes

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