Chloroform → HCID 67915830, compound

HRID 1165038Notes

Reaction equation

HRID 1165038 reaction equation
[NH2:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16]O)[CH2:11][C@H:10]2[O:18][CH3:19])=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1.[Cl:25]C(Cl)Cl.S(Cl)(Cl)=O>N1C=CC=CC=1>[OH2:7].[NH2:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][Cl:25])[CH2:11][C@H:10]2[O:18][CH3:19])=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 67915710HCID 67915710, compound

Product 1

HCID 67915830HCID 67915830, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 5.01 parts of cis-4-amino-5-chloro-N-[1-(2-hydroxyethyl)-3-methoxy-4-piperidinyl]-2-methoxybenzamide in 112.5 parts of trichloromethane were added 1.33 parts of pyridine and 2 parts of thionyl chloride. The whole was stirred and heated for 7 hours at 50° C. and subsequently stirred overnight at room temperature. The reaction mixture was washed with a sodium hydroxide solution and water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated, yielding 9 parts of cis-4-amino-5-chloro-N-[1-(2-chloroethyl)-3- methoxy-4-piperidinyl]-2-methoxybenzamide monohydrate as a residue (interm. 15).

Workup

  1. washThe reaction mixture was washed with a sodium hydroxide solution and water
  2. extractionThe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f6b001de6c924b219357877f1cf1fc93
Source dataset
uspto-grants-1990_03
Patent number
US04906643

Reaction notes

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