Formaldehyde → 2-Dimethylamino-1-phenyl-1-propanone hydrochloride

HRID 273660Notes

Reaction equation

HRID 273660 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:10]=O.[ClH:12].[CH3:13][NH:14][CH3:15]>>[ClH:12].[CH3:13][N:14]([CH:2]([CH3:10])[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3])[CH3:15]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 7410AcetophenoneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 30840612-Dimethylamino-1-phenyl-1-propanone hydrochlorideYield 29%

Procedure

A mixture of acetophenone (100 g), paraformaldehyde (25 g) and dimethylamine hydrochloride (68 g) was vigorously stirred and pumped through the CMR (23 ml/min.; 180°-90° C.; 400 kPa). The product tended to crystallise rapidly when cooled, so was collected by passing the hot effluent into a flask which was cooled in ice-water. Analysis by 1H nmr indicated a 44% conversion of acetophenone to product, which was isolated in 29% yield. By conventional methodology8, a crude yield of 71% can be obtained after 2 hours at reflux followed by overnight refrigeration.

Workup

  1. custompumped through the CMR (23 ml/min.; 180°-90° C.; 400 kPa)
  2. customto crystallise rapidly when
  3. temperaturecooled
  4. customso was collected
  5. temperaturewas cooled in ice-water
  6. customwhich was isolated in 29% yield
  7. customBy conventional methodology8, a crude yield of 71% can be obtained after 2 hours
  8. temperatureat reflux

Sources & evidence

ORD record
ord-a0c11db456124aeeace7192f353d2156
Source dataset
uspto-grants-1995_02
Patent number
US05387397

Reaction notes

Loading…