Sulfuric Acid → HCID 69111440, compound

HRID 1590085Notes

Reaction equation

HRID 1590085 reaction equation
[CH3:1][N:2]([CH3:21])[CH:3]([CH3:20])[CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:6]#[N:7].S(=O)(=O)(O)[OH:23].C(Cl)[Cl:28].[OH-].[Na+]>O>[ClH:28].[CH3:21][N:2]([CH3:1])[C@H:3]([CH3:20])[CH2:4][C@@:5]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:6]([NH2:7])=[O:23]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 11076813HCID 11076813, compound

Product 1

HCID 69111440HCID 69111440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A mixture of 4-dimethylamino-2-phenyl-2-(2-pyridyl)-valeronitrile (50.0 g), water (2.74 g) and sulfuric acid (50 ml) was reacted at 100-105° C. for 2 hours. The reaction mixture was then cooled, diluted with cold water (100 ml) and poured into a mixture of methylene chloride (400 ml) and water(500 ml). The aqueous layer was adjusted to pH 12.5 with 24% aqueous sodium hydroxide solution. The organic layer was taken, washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. To this were added isopropyl alcohol (75 ml), acetone (175 ml) and concentrated hydrochloric acid (10.87 g) and the mixture was stirred for 10 minutes. Then, seed crystals (0.05 g) were added and the mixture was further stirred at 25-30° C. for 1 hour and, then, at -5° to -10° C. for another 1 hour. The resulting crystals were recovered by filtration, washed with methylene chloride and dried to give (±)-(2R*,4R*)-4-dimethylamino-2-phenyl-2-(2-pyridyl)valeramide hydrochloride (26.9 g).

Workup

  1. customwas reacted at 100-105° C. for 2 hours
  2. temperatureThe reaction mixture was then cooled
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additionTo this were added isopropyl alcohol (75 ml), acetone (175 ml) and concentrated hydrochloric acid (10.87 g)
  6. additionThen, seed crystals (0.05 g) were added
  7. stirringthe mixture was further stirred at 25-30° C. for 1 hour
  8. waitat -5° to -10° C. for another 1 hour
  9. filtrationThe resulting crystals were recovered by filtration
  10. washwashed with methylene chloride
  11. customdried

Sources & evidence

ORD record
ord-ff63a8506b4c4da7a81692bade6e0148
Source dataset
uspto-grants-1993_04
Patent number
US05202331

Reaction notes

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