Hydrochloric Acid → HCID 22464567, compound

HRID 1935462Notes

Reaction equation

HRID 1935462 reaction equation
Cl[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]Cl.Cl.[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH3:20]>ClC1C=CC=CC=1>[CH3:20][C:11]1[CH:12]=[CH:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]=1[N:9]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9533Bis(2-chloroethyl)amineHCID 167332-Methyl-1-naphthylamine

Product 1

HCID 22464567HCID 22464567, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

14.7 g (82.7 mmol) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mmol) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene and the mixture was boiled under nitrogen and at reflux for 90 h. The mixture was then evaporated and the residue was partitioned between methylene chloride and water at pH=9, and the organic phase was evaporated after having been dried. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia, 85/13/2). 11.6 g (62%) of product were isolated.

Workup

  1. temperatureat reflux for 90 h
  2. customThe mixture was then evaporated
  3. customthe residue was partitioned between methylene chloride and water at pH=9
  4. customthe organic phase was evaporated
  5. customafter having been dried
  6. customThe crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia, 85/13/2)

Sources & evidence

ORD record
ord-10274d72223e427dbb62576613015e7a
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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