Hydrochloric Acid → HCID 13677833, compound

HRID 345584Notes

Reaction equation

HRID 345584 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C@@H:13]([NH:16]C(=O)C3C=CC=CC=3)[C@H:12]([O:25][CH3:26])[CH2:11]2)=[CH:4][CH:3]=1.Cl>>[F:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C@@H:13]([NH2:16])[C@H:12]([O:25][CH3:26])[CH2:11]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 15096772HCID 15096772, compound

Product 1

HCID 13677833HCID 13677833, compoundYield 79%

Conditions

Temperature
140 °C

Procedure

A mixture of 5.1 parts of trans-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]benzamide and 84 parts of a concentrated hydrochloric acid solution was stirred and refluxed for 22 hours in an oil-bath at 140° C. The reaction mixture was cooled, filtered and the filter-cake was washed with water. The filtrate was evaporated. The residue was taken up in 35 parts of water and the whole was treated with sodium hydroxide solution. The product was extracted three times with methylbenzene. The combined extracts were washed with a small amount of water, dried, filtered and evaporated, yielding 2.9 parts (79%) of trans-1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinamine as a residue (intermediate 121).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe filter-cake was washed with water
  4. customThe filtrate was evaporated
  5. additionthe whole was treated with sodium hydroxide solution
  6. extractionThe product was extracted three times with methylbenzene
  7. washThe combined extracts were washed with a small amount of water
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-9365762764af475cb5b8599efcb3001f
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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