Hydrochloric Acid → HCID 20226373, compound

HRID 1731998Notes

Reaction equation

HRID 1731998 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:6]([CH2:8][CH2:9][C:10](O)=O)=[O:7])#[N:2].[CH2:22]=[O:23].[OH-:24].[Na+].Cl>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:6]([CH:8]1[O:24][C:22](=[O:23])[CH2:10][CH2:9]1)=[O:7])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 20164996HCID 20164996, compound

Product 1

HCID 20226373HCID 20226373, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10 g of 3-(3-cyano-4-morpholino-benzoyl)-propionic acid are stirred together with 2.98 g of 35% formaldehyde solution and 76.4 ml of 0.5N sodium hydroxide solution for 16 hours at room temperature. The reaction mixture, whilst being cooled with ice-water and stirred, is then rendered acid with concentrated hydrochloric acid, and is stirred for a further 16 hours at room temperature. Ethyl acetate is afterwards added until two clear phases are formed; the aqueous phase is subsequently separated, and extracted with ethyl acetate. The organic phases are washed twice with 2N sodium carbonate solution, with water and with brine; they are then dried over sodium sulfate and concentrated by evaporation. The 4-(3-cyano-4-morpholino-benzoyl)-butyrolactone obtained as an oily residue is used directly in the following stage.

Workup

  1. stirringis stirred for a further 16 hours at room temperature
  2. customare formed
  3. customthe aqueous phase is subsequently separated
  4. extractionextracted with ethyl acetate
  5. washThe organic phases are washed twice with 2N sodium carbonate solution, with water and with brine
  6. dry with materialthey are then dried over sodium sulfate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-491a44569bce4a799525e2905cd076f2
Source dataset
uspto-grants-1986_11
Patent number
US04624951

Reaction notes

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