Hydrochloric Acid → 1,2-Diamino-3-(4-chlorophenyl)propane

HRID 246887Notes

Reaction equation

HRID 246887 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([NH2:11])=O)[NH2:8])=[CH:4][CH:3]=1.Cl.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>O1CCCC1>[NH2:11][CH2:9][CH:7]([NH2:8])[CH2:6][C:5]1[CH:12]=[CH:13][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 186106874-ChlorophenylalanineamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1593051,2-Diamino-3-(4-chlorophenyl)propane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.1 mole (20 grams) of 4-chlorophenylalanineamide or hydrochloride were added in small portions to a well stirred suspension of 0.3 mole of LiAlH4 in 250 ml of dry tetrahydrofuran. The mixture was stirred for 24 hours under reflux and subsequently under ice cooling hydrolyzed dropwise with 1.2 moles of H2O. After stirring at room temperature for an additional hour it was filtered off from the hydrolysis products accumulating as a slime-like solid. This residue was extracted for 24 hours with 127 ml of tetrahydrofuran. Filtrate and extract were combined.

Workup

  1. stirringThe mixture was stirred for 24 hours
  2. stirringAfter stirring at room temperature for an additional hour it
  3. filtrationwas filtered off from the hydrolysis products
  4. extractionThis residue was extracted for 24 hours with 127 ml of tetrahydrofuran
  5. extractionFiltrate and extract

Sources & evidence

ORD record
ord-ac848ebbed3c4d4b88a40679232c152d
Source dataset
uspto-grants-1987_11
Patent number
US04704464

Reaction notes

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