HCID 20378453, compound → HCID 18981157, compound

HRID 2052018Notes

Reaction equation

HRID 2052018 reaction equation
C([NH:4][CH2:5][CH:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][NH:9]C(=O)C)(=O)C>[OH-].[Na+]>[NH2:4][CH2:5][CH:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:7]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:8][NH2:9]

Participants

3

Reactant 1

HCID 20378453HCID 20378453, compound

Product 1

HCID 18981157HCID 18981157, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

385.7 g (1.19 mols) of N,N'-diacetyl-2,3-diphenyl-1,4-diaminobutane in 715 ml of 5 N sodium hydroxide solution are heated to 200° C. in an autoclave for 16 hours. After cooling, the mixture is extracted with 1,800 ml of chloroform. Further extraction with 2 times 200 ml of chloroform and concentration of the extracts gives 285.4 g of crude product, which is recrystallised from 2.6 l of benzene. Yield: 258.5 g of 1,4-diamino-2,3-diphenylbutane; melting point: 144°-145° C. A further 15.1 g of substance having a melting point of 144°-145° C. are obtained by concentrating the mother liquor; the total yield is thus 273.6 g (95.7% of theory). For analysis, 1.0 g is recrystallised from 10 ml of benzene. Yield: 0.88 g; melting point: 144°-145° C; meso form.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with 1,800 ml of chloroform
  3. extractionFurther extraction with 2 times 200 ml of chloroform and concentration of the extracts

Sources & evidence

ORD record
ord-4a8808252b9740e696a05d463e9e9b62
Source dataset
uspto-grants-1980_01
Patent number
US04182832

Reaction notes

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