4-Methylmorpholine → 126233-80-5

HRID 1082056Notes

Reaction equation

HRID 1082056 reaction equation
CN1CC[O:5][CH2:4]C1.[CH3:8][C@@H:9]1[NH:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[C:19]([NH2:20])[C:12]=2[NH:11][CH2:10]1.ClC(OC(Cl)(Cl)Cl)=O>ClCCl>[CH3:8][C@@H:9]1[NH:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[C:19]3[NH:20][C:4](=[O:5])[N:11]([C:12]=23)[CH2:10]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10426DiphosgeneHCID 118299831H-1,4-Benzodiazepin-9-amine, 2,3,4,5-tetrahydro-3-methyl-, (S)-

Product 1

HCID 452819126233-80-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

300 ml of dichloromethane and 22.8 ml of 4-methylmorpholine are added to 12.7 g (0.072 mol) of (S)-3-methyl-2,3,4,5-tetrahydro-(1H)-1,4-benzodiazepin-9-amine. The mixture is then poured into a solution of 9.1 ml (0.0072 mol) of trichloromethyl chloroformate in 340 ml of dichloromethane cooled beforehand with an ice bath. The mixture is left stirring for 10 minutes at 0° C. and then for 20 minutes at room temperature. The solvent is evaporated under vacuum and the residue taken up in 200 ml of water and 34 ml of dioxane. The mixture is heated in a water bath for 45 minutes and then a concentrated aqueous ammonia solution is added. The mixture is left to cool, is sucked dry, is washed with water and is dried under vacuum. There are obtained 11.5 g of product which is recrystallized from boiling water. There are obtained 7.6 g of product which is used as is in the following stage.

Workup

  1. temperaturecooled beforehand with an ice bath
  2. waitThe mixture is left
  3. waitfor 20 minutes at room temperature
  4. customThe solvent is evaporated under vacuum
  5. temperatureThe mixture is heated in a water bath for 45 minutes
  6. additiona concentrated aqueous ammonia solution is added
  7. waitThe mixture is left
  8. temperatureto cool
  9. customis sucked dry
  10. washis washed with water
  11. customis dried under vacuum

Sources & evidence

ORD record
ord-e0c3c32e6a4a4dad8ed99520f500f0a5
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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