Hydrochloric Acid → HCID 22464567, compound

HRID 276817Notes

Reaction equation

HRID 276817 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 mM) of bis(2-chloroethyl)amine×HCl were added to 13.0 g (82.7 mM) of 1-amino-2-methylnaphthalene in 100 ml of chlorobenzene and refluxed under nitrogen for 90 h. The mixture was then concentrated and partitioned between methylene chloride and water at pH=9, and the organic phase was dried and concentrated. The crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2. 11.6 g (62%) of product were isolated.

Workup

  1. temperaturerefluxed under nitrogen for 90 h
  2. concentrationThe mixture was then concentrated
  3. custompartitioned between methylene chloride and water at pH=9
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, mobile phase/THF/methanol/ammonia 85/13/2

Sources & evidence

ORD record
ord-4bf4adec3bb0413ea738f13c454775a0
Source dataset
uspto-grants-2002_03
Patent number
US06355647B1

Reaction notes

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