Hydrochloric Acid → HCID 22241240, compound

HRID 584615Notes

Reaction equation

HRID 584615 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH:7]2[CH2:11][CH2:10][N:9]([CH2:12][CH:13]([OH:26])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:22]C(=O)C)[CH2:8]2)=[CH:4][CH:3]=1.[ClH:29]>CO.C(OCC)C>[ClH:1].[ClH:29].[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH2:14][CH:13]([OH:26])[CH2:12][N:9]1[CH2:10][CH2:11][CH:7]([O:6][C:5]2[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10201260HCID 10201260, compound

Product 1

HCID 22241240HCID 22241240, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
102.5 °C

Procedure

A mixture of N-(2-{3-[3-(4-chlorophenoxy)-1-pyrrolidinyl]-2-hydroxypropoxy}phenyl)acetamide (0.95 g, 2.34 mmol) and concentrated hydrochloric acid (25 mL) was heated (100-105° C.) for 3 hours then allowed to stand at room temperature overnight. The mixture was concentrated at reduced pressure to a third of its volume basified with saturated sodium hydrogen carbonate. The resulting suspension was extracted twice with ethyl acetate. The organic extracts were dried, the solvent was evaporated at reduced pressure to give a pale brown oil. This oil was dissolved in a minimum amount of methanol, diluted with ethyl ether and the product precipitated by addition of HCl-saturated ethyl ether. The product was filtered to afford the subtitle product (0.93 g, 91.2%).

Workup

  1. concentrationThe mixture was concentrated at reduced pressure to a third of its volume
  2. extractionThe resulting suspension was extracted twice with ethyl acetate
  3. customThe organic extracts were dried
  4. customthe solvent was evaporated at reduced pressure
  5. customto give a pale brown oil
  6. customthe product precipitated by addition of HCl-saturated ethyl ether
  7. filtrationThe product was filtered

Sources & evidence

ORD record
ord-be991649e3a04c19ad49fc86ccf8da5d
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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