Calcium Carbonate → 3-((3-Hydroxypropyl)methylamino)benzonitrile

HRID 591141Notes

Reaction equation

HRID 591141 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].Cl[CH2:12][CH2:13][CH2:14][OH:15].C([O-])([O-])=O.[Ca+2]>O>[OH:15][CH2:14][CH2:13][CH2:12][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 123133-Chloro-1-propanolHCID 177940363-(Methylamino)benzonitrile

Product 1

HCID 617014023-((3-Hydroxypropyl)methylamino)benzonitrileYield 125.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-methylaminobenzonitrile (17.34 g, 0.13 mol, 1.0 eq), 3-chloropropanol (49.70 g, 0.53 mol, 4.0 eq) and CaCO3 (52.50 g, 0.53 mol, 4.0 eq) are added into water (230 ml) at room temperature, the mixture is refluxed at elevated temperature for 40 h, and cooled, filtered and extracted with ethyl acetate (200 ml*3). The organic phases are combined, washed with water (100 ml*2), washed with saturated brine twice, dried over anhydrous sodium sulfate and concentrated to give a light yellow oily crude product (31.08 g). The residue could be used directly in next step without purification.

Workup

  1. temperaturethe mixture is refluxed at elevated temperature for 40 h
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionextracted with ethyl acetate (200 ml*3)
  5. washwashed with water (100 ml*2)
  6. washwashed with saturated brine twice
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1723ece1455f45aba67d49edc065cfe3
Source dataset
uspto-grants-2016_01
Patent number
US09238632B2

Reaction notes

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