Acetone → 2-(N-isopropylamino)-4-methylbenzophenone

HRID 1834848Notes

Reaction equation

HRID 1834848 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[C:4]([NH2:16])[CH:3]=1.[CH3:17][C:18]([CH3:20])=O.[BH4-].S(=O)(=O)(O)O>O>[CH:18]([NH:16][C:4]1[CH:3]=[C:2]([CH3:1])[CH:15]=[CH:14][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])([CH3:20])[CH3:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 28123Borohydride2×HCID 786512-Amino-4-methylbenzophenone

Product 1

HCID 128985342-(N-isopropylamino)-4-methylbenzophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Examples 1-19 as recorded in the following Table I represent trials in which the amount of 4-methyl-2-aminobenzophenone (a compound III in amount of 21.1 grs. or 0.1 mol) is held constant and the amount of other reaction system components including acetone (the compound III), borohydride (sodium borohydride), acid (sulfuric acid) and water are varied. In these examples, the reaction system is maintained at 20°-25° C. throughout the reaction and the rate of addition of the borohydride is controlled accordingly, such addition requiring in most cases about 60 minutes, after which the reaction system is stirred for an additional 60 minutes, followed by filtering. The filtrate is concentrated and the residue dissolved in about 88 mls. of heptane and the resulting solution extracted first with 20 mls. of 4N. ammonium hydroxide solution, then three times each with 10 mls. of 2N. sulfuric acid, and then washed with 10 mls. of 0.5N sulfuric acid. The heptane is distilled off to obtain the desired 2-(N-isopropylamino)-4-methylbenzophenone which boils at 180° -185° C./5 mm Hg.

Workup

  1. customis maintained at 20°-25° C. throughout the reaction
  2. additionsuch addition
  3. customrequiring in most cases about 60 minutes
  4. filtrationby filtering
  5. concentrationThe filtrate is concentrated
  6. dissolutionthe residue dissolved in about 88 mls
  7. extractionof heptane and the resulting solution extracted first with 20 mls
  8. washsulfuric acid, and then washed with 10 mls
  9. distillationThe heptane is distilled off

Sources & evidence

ORD record
ord-32188f8839f24aa4b6f0d833be52badb
Source dataset
uspto-grants-1978_01
Patent number
US04071557

Reaction notes

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