Water → HCID 710520, compound

HRID 378752Notes

Reaction equation

HRID 378752 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[OH2:16]>CC1CCCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([N:10]2[CH2:15][CH2:14][O:16][CH2:12][CH2:11]2)[N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 8083Morpholine

Product 1

HCID 710520HCID 710520, compound

Reagents, catalysts & solvents 1

HCID 7962MethylcyclohexaneSolvent

Procedure

70 g of p-chlorobenzaldehyde and 105 g of morpholine were heated to boiling in 260 g of methylcyclohexane in a water separator. Over the course of 45 minutes, 8.4 ml of water were removed azeotropically. The mixture was left to cool with slow stirring. At 58° C., the solution was seeded, and very fine crystals slowly precipitated out. The mixture was cooled in an ice bath to +5° C. After a post-stirring time of 1 hour, the solid which had precipitated out was filtered off with suction. The white product was washed with 2×50 ml of methylcyclohexane and dried overnight in a drying cabinet at 20° C. and 100 mbar. 129.2 g of product were obtained in the form of white crystals (87% of theory).

Workup

  1. customOver the course of 45 minutes, 8.4 ml of water were removed azeotropically
  2. waitThe mixture was left
  3. temperatureto cool with slow stirring
  4. customAt 58° C.
  5. customvery fine crystals slowly precipitated out
  6. temperatureThe mixture was cooled in an ice bath to +5° C
  7. customAfter a post-stirring time of 1 hour, the solid which had precipitated out
  8. filtrationwas filtered off with suction
  9. washThe white product was washed with 2×50 ml of methylcyclohexane
  10. customdried overnight in a drying cabinet at 20° C.

Sources & evidence

ORD record
ord-745b32d32d88497f9e058ee30296b5c4
Source dataset
uspto-grants-2001_10
Patent number
US06296788B1

Reaction notes

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