Morpholine → HCID 59543863, compound

HRID 1924015Notes

Reaction equation

HRID 1924015 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH2:6][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 189911424-Chloro-2,5-difluorobenzaldehyde

Product 1

HCID 59543863HCID 59543863, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-Chloro-2,5-difluorobenzaldehyde (1 g, 5.66 mmol), morpholine (0.490 ml, 5.66 mmol) and sodium triacetoxyborohydride (1.741 g, 8.21 mmol) were mixed in dichloroethane (17 ml). The mixture was stirred at ambient temperature under argon atmosphere for 3 days. NaHCO3 (aq., sat, 25 ml) was added. The mixture was extracted with dichloromethane (×3). The combined organic phase were dried over MgSO4 filtered and concentrated in vacuo to give 4-(4-chloro-2,5-difluorobenzyl)morpholine (0.600 g, 43%) as a liquid.

Workup

  1. extractionThe mixture was extracted with dichloromethane (×3)
  2. dry with materialThe combined organic phase were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbc8a008b11b4d41b3bc760b39d3e662
Source dataset
uspto-grants-2012_05
Patent number
US08178529B2

Reaction notes

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