Sodium Hydroxide → HCID 70451836, compound

HRID 1381267Notes

Reaction equation

HRID 1381267 reaction equation
[OH:1][C@H:2]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][N:4]([CH2:16][C@H:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[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+]>O1CCCC1>[OH:24][C@H:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:16][N:4]([CH2:3][C@H:2]([OH:1])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:5][CH2:6][CH2:7][C:8]1[S:12][C:11]([CH2:13][NH2:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54086303HCID 54086303, compound

Product 1

HCID 70451836HCID 70451836, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

850 mg of 5-[3-[bis-[(R)-β-hydroxyphenethyl]amino]propyl]-2-thiophenecarboxamide and 300 mg of lithium aluminum hydride were boiled at reflux for 1.5 hours in 60 ml of tetrahydrofuran. The mixture was treated cautiously with 2N sodium hydroxide solution and extracted three times with ether. The ether solutions were washed neutral with water, dried and evaporated. Chromatography of the residue on silica gel with methanol gave 650 mg of 5-[3-[bis-[(R)-β-hydroxyphenethyl]amino]propyl]-2-aminomethyl-thiophene.

Workup

  1. extractionextracted three times with ether
  2. washThe ether solutions were washed neutral with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-9ea294fc163b4547b0089b98657d8c2b
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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