Dichloromethane → Morpholinium, 4-(chloromethylene)-, chloride

HRID 1589253Notes

Reaction equation

HRID 1589253 reaction equation
C([N:3]1[CH2:8][CH2:7]C[CH2:5][CH2:4]1)=O.S(Cl)([Cl:11])=[O:10].[CH2:13]([Cl:15])Cl>C1(C)C=CC=CC=1>[Cl-:11].[Cl:15][CH:13]=[N+:3]1[CH2:4][CH2:5][O:10][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 174291-PiperidinecarboxaldehydeHCID 24386Thionyl Chloride

Product 1

HCID 11355716Morpholinium, 4-(chloromethylene)-, chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
56 °C

Procedure

Under dry nitrogen, N-formyl piperidine (124 gm, 1.10 mol), rapidly stirring at -4° C., is treated dropwise over the course of 30 minutes with thionyl chloride (144 gm, 1.21 mol), the temperature being maintained below 0° C. with ice-methanol cooling. The resulting solution is warmed slowly to 56° C. over 80 minutes with the application of vacuum (at about 30 mm). A mixture of methylene chloride 10 ml and toluene (40 ml) is added, and the resulting slurry is concentrated to dryness (37° C., about 30 mm vacuum). This stripping procedure is repeated, and final concentration is accomplished by the application of higher (about 5 mm) vacuum (30°-42° C., 30 min), to yield solid N-(chloromethylene)-morpholinium chloride.

Workup

  1. additionis added
  2. concentrationthe resulting slurry is concentrated to dryness (37° C., about 30 mm vacuum)
  3. concentrationfinal concentration
  4. customis accomplished by the application of higher (about 5 mm) vacuum (30°-42° C., 30 min)

Sources & evidence

ORD record
ord-be32a7f02ccd4127960dd0c222a95e77
Source dataset
uspto-grants-1986_02
Patent number
US04568741

Reaction notes

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