Hydrochloric Acid → HCID 13677860, compound

HRID 846757Notes

Reaction equation

HRID 846757 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8]C(=O)C2C=CC=CC=2)[CH2:6][CH2:5][N:4]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3]1.Cl>>[NH2:8][C@@H:7]1[CH2:6][CH2:5][N:4]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:3][C@H:2]1[OH:1]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 15096758HCID 15096758, compound

Product 1

HCID 13677860HCID 13677860, compound

Procedure

A mixture of 15 parts of trans-N-[3-hydroxy-1-(phenylmethyl)-4-piperidinyl]benzamide and 204 parts of a concentrated hydrochloric acid solution was stirred and refluxed for 18 hours. The reaction mixture was filtered and the filtrate was treated with sodium hydroxide. Upon cooling in an ice-bath, the addition of sodium hydroxide was continued till turbid. The product was extracted three times with 180 parts of methylbenzene. The combined extracts were dried, filtered and evaporated. The oily residue was dissolved in trichloromethane. The solution was washed with a small amount of water, dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue solidified on triturating in petroleumether. The product was filtered off and dried, yielding 3.8 parts of trans-4-amino-1-(phenylmethyl)-3-piperidinol; mp. 74.1° C. (intermediate 72).

Workup

  1. temperaturerefluxed for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate was treated with sodium hydroxide
  4. temperatureUpon cooling in an ice-bath
  5. additionthe addition of sodium hydroxide
  6. extractionThe product was extracted three times with 180 parts of methylbenzene
  7. customThe combined extracts were dried
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe oily residue was dissolved in trichloromethane
  11. washThe solution was washed with a small amount of water
  12. customdried
  13. filtrationfiltered
  14. customevaporated
  15. customThe oily residue was purified by column-chromatography over silica gel using
  16. additiona mixture of trichloromethane and methanol
  17. customThe pure fractions were collected
  18. customthe eluent was evaporated
  19. customon triturating in petroleumether
  20. filtrationThe product was filtered off
  21. customdried

Sources & evidence

ORD record
ord-feeec42069f944989fcfc9a6affe1237
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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