Water → HCID 54482871, compound

HRID 1906658Notes

Reaction equation

HRID 1906658 reaction equation
[OH:1][C@H:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]([NH2:15])=O)=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[NH2:15][CH2:13][C:11]1[S:12][C:8]([CH2:7][CH2:6][CH2:5][NH:4][CH2:3][C@H:2]([OH:1])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53677255HCID 53677255, compound

Product 1

HCID 54482871HCID 54482871, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.58 g of 5-[3-[[(R)-β-hydroxyphenethyl]amino]propyl]-2-thiophenecarboxamide were treated portionwise in 129 ml of tetrahydrofuran under argon with 1.29 g of lithium aluminium hydride and the mixture was boiled at reflux for 3.25 hours. Then, while cooling, there were cautiously added 34 ml of 2N sodium hydroxide solution and subsequently 400 ml of water and the mixture was extracted three times with chloroform. The chloroform solutions were washed neutral with water and dilute sodium chloride solution, dried and evaporated in vacuo. Chromatography on silica gel with methanol and 0.5% concentrated ammonia and crystallization from acetonitrile/ether gave 914 mg of (R)-α-[[[3-[5-(aminomethyl)-2-thienyl]propyl]amino]methyl]benzyl alcohol of melting point 64°-65°. [α]D =-18° (c=0.1% in dioxane); UV: ε240 =9080.

Workup

  1. temperatureat reflux for 3.25 hours
  2. temperatureThen, while cooling
  3. extractionthe mixture was extracted three times with chloroform
  4. washThe chloroform solutions were washed neutral with water and dilute sodium chloride solution
  5. customdried
  6. customevaporated in vacuo
  7. customChromatography on silica gel with methanol and 0.5% concentrated ammonia and crystallization from acetonitrile/ether

Sources & evidence

ORD record
ord-cbea0afc56e74f559b1e1dc72851ae58
Source dataset
uspto-grants-1987_03
Patent number
US04652679

Reaction notes

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