Ammonium Chloride → HCID 20359373, compound

HRID 2083168Notes

Reaction equation

HRID 2083168 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].C([Li])CCC.[CH3:17][N:18]([CH3:29])[CH2:19][CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:29][N:18]([CH3:17])[CH2:19][CH2:20][C:21]([OH:22])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 75111N-methyl-2-toluamideHCID 770423-(Dimethylamino)-1-phenyl-1-propanoneHCID 178418339Butyllithium

Product 1

HCID 20359373HCID 20359373, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

To a flask equipped with a stirrer, dropping funnel, condenser and gas inlet tube maintained under a nitrogen atmosphere there is added at room temperature 40.0 g. (0.28 mole) of o-methyl-N-methyl benzamide and 250 ml. of anhydrous tetrahydrofuran. The reaction flask is immersed in an ice bath and cooled to an internal temperature of 5° C. Stirring is initiated and 360 ml. of 1.6 M. n-butyllithium (0.616 mole) in hexane is added dropwise for about 1 hour maintaining the temperature below 8° C. The resulting red dilithio salt (compound VIII) is stirred at 5° C. for 1 additional hour and the reaction flask is then immersed in a dry-ice acetone bath and cooled to an internal temperature of -30° C. To the cold reaction mixture a solution of 49.7 g. (0.28 mole) 3-dimethylaminopropiophenone in 140 ml. anhydrous tetrahydrofuran is added dropwise in ca. 45 minutes maintaining the temperature between -30° and -20° C. The resulting reaction mixture is stirred at -25° C. for 1 hour, allowed to warm to -10° C. in ca. 1 hour, and then treated with 200 ml. of saturated aqueous ammonium chloride while maintaining the temperature below 0° C. The resulting solid in filtered, washed thoroughly with water and recrystallized from methylene chloride-ether (1:1) to give 2-(β-[2-dimethylaminoethyl]-β-hydroxyphenethyl)-N-methylbenzamide; m.p. 139.5° to 140.5° C.

Workup

  1. customTo a flask equipped with a stirrer
  2. temperaturemaintained under a nitrogen atmosphere
  3. additionthere is added at room temperature 40.0 g
  4. customThe reaction flask is immersed in an ice bath
  5. temperaturemaintaining the temperature below 8° C
  6. customthe reaction flask is then immersed in a dry-ice acetone bath
  7. temperaturecooled to an internal temperature of -30° C
  8. customTo the cold reaction mixture a solution of 49.7 g
  9. temperaturemaintaining the temperature between -30° and -20° C
  10. customThe resulting reaction mixture
  11. stirringis stirred at -25° C. for 1 hour
  12. temperatureto warm to -10° C. in ca. 1 hour
  13. additiontreated with 200 ml
  14. filtrationThe resulting solid in filtered
  15. washwashed thoroughly with water
  16. customrecrystallized from methylene chloride-ether (1:1)

Sources & evidence

ORD record
ord-b7de1b19516348b6bec9548ff6394d47
Source dataset
uspto-grants-1978_04
Patent number
US04083997

Reaction notes

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