Methane → 3-Cyano-2-morpholino-5-(pyrid-4-yl)pyridine

HRID 1590767Notes

Reaction equation

HRID 1590767 reaction equation
O.Cl.[C:3]([C:5]1[C:6]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:10]=1)#[N:4].C>O>[C:3]([C:5]1[C:6]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:7][CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)[CH:10]=1)#[N:4]

Participants

4

Reactant 2

HCID 297MethaneHCID 13632831HCID 13632831, compound

Product 1

HCID 1309523-Cyano-2-morpholino-5-(pyrid-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

5.3 kg 3-cyano-2-morpholino-5-(pyrid-4-yl)-pyridine hydrochloride monohydrate is suspended in 40 l water and the suspension is heated to 50° C. 0.5 kg activated charcoal is added and filtered off with suction after 15 minutes of stirring and washed with water. The filtrate is cooled to 30° C. While stirring, about 2.7 l concentrated sodium hydroxide solution is allowed to run in over a period of one hour at this temperature until pH 8-9. The crystalline material is centrifuged off and washed with total of 30 l water. The yield is 4.1 kg (93.2% of the theoretical yield), with a melting point of 126° C.-128° C. The bulk density of the material, after is was pulverized in a mortar, was about 360 g/l.

Workup

  1. additionis added
  2. filtrationfiltered off with suction after 15 minutes
  3. washwashed with water
  4. temperatureThe filtrate is cooled to 30° C
  5. stirringWhile stirring
  6. customto run in over a period of one hour at this temperature until pH 8-9
  7. washwashed with total of 30 l water
  8. customThe yield is 4.1 kg (93.2% of the theoretical yield), with a melting point of 126° C.-128° C

Sources & evidence

ORD record
ord-1d1b6d8b991e45ff8c8427184bedad83
Source dataset
uspto-grants-1993_04
Patent number
US05204464

Reaction notes

Loading…