Hexamethylenetetramine → Acetamide, 2-amino-N-(2-(7-methoxy-1-naphthalenyl)ethyl)-, monohydrochloride

HRID 483398Notes

Reaction equation

HRID 483398 reaction equation
C1N2CN3CN(C2)C[N:2]1C3.[CH3:11][O:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[C:20]2[CH2:23][CH2:24][NH:25][C:26](=[O:29])[CH2:27]Br)=[CH:15][CH:14]=1.C(Cl)(Cl)[Cl:31]>>[ClH:31].[CH3:11][O:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[C:20]2[CH2:23][CH2:24][NH:25][C:26](=[O:29])[CH2:27][NH2:2])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6212Chloroform2×HCID 3071636Acetamide, 2-bromo-N-(2-(7-methoxy-1-naphthalenyl)ethyl)-

Product 1

HCID 3071650Acetamide, 2-amino-N-(2-(7-methoxy-1-naphthalenyl)ethyl)-, monohydrochloride

Procedure

0.012 mol of hexamethylenetetramine is dissolved under magnetic agitation in 15 ml of chloroform, and 0.01 mol of N-[2-(7-methoxynaphth-1-yl)ethyl]-2-bromoacetamide obtained in Example 9 dissolved in 20 ml of chloroform are introduced. The mixture is refluxed for 100 hours, spun down and dried. The precipitate is introduced into a ground glass flask and 150 ml of alcohol and 30 ml of concentrated hydrochloric acid are added. The mixture is refluxed for two hours, and then the solvent is evaporated and the residue is recrystallized in alcohol at 90° C.

Workup

  1. additionare introduced
  2. temperatureThe mixture is refluxed for 100 hours
  3. customdried
  4. additionThe precipitate is introduced into a ground glass flask
  5. addition150 ml of alcohol and 30 ml of concentrated hydrochloric acid are added
  6. temperatureThe mixture is refluxed for two hours
  7. customthe solvent is evaporated
  8. customthe residue is recrystallized in alcohol at 90° C.

Sources & evidence

ORD record
ord-bf3bba05135c4cbd8f21cd468803e105
Source dataset
uspto-grants-1993_07
Patent number
US05225442

Reaction notes

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