Hexamethylenetetramine → HCID 20337667, compound

HRID 2052195Notes

Reaction equation

HRID 2052195 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23]Br)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C1N2CN3CN(C2)C[N:27]1C3.C(Cl)(Cl)[Cl:37]>>[ClH:37].[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23][NH2:27])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6212ChloroformHCID 539946982-Bromo-1-[4-(tetradecyloxy)phenyl]ethan-1-one

Product 1

HCID 20337667HCID 20337667, compoundYield 95%

Procedure

88 g of p-tetradecyloxy-ω-bromoacetophenone are dissolved in 320 ml of anhydrous chloroform. 30.4 g of urotropine are added at room temperature. The solution heats up spontaneously. It is then stirred for 2 hours at room temperature. The chloroform is evaporated off and the solid residue is triturated with acetone. The crystalline precipitate is suction filtered and washed several times with acetone. The crude product is then introduced into a solution of 140 ml of concentrated hydrochloric acid in 1000 ml of ethanol and stirred for 24 hours at room temperature. The product is suction filtered and washed with a mixture of ethanol and concentrated hydrochloric acid (7:1). 80 g =95% of p-tetradecyloxy-ω-aminoacetophenone-hydrochloride melting at 190° to 195° C. are obtained.

Workup

  1. customThe chloroform is evaporated off
  2. customthe solid residue is triturated with acetone
  3. filtrationfiltered
  4. washwashed several times with acetone
  5. additionThe crude product is then introduced into a solution of 140 ml of concentrated hydrochloric acid in 1000 ml of ethanol
  6. stirringstirred for 24 hours at room temperature
  7. filtrationfiltered
  8. washwashed with a mixture of ethanol and concentrated hydrochloric acid (7:1)

Sources & evidence

ORD record
ord-26dcca492c964e50af4a71761917c409
Source dataset
uspto-grants-1980_01
Patent number
US04183752

Reaction notes

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