Hydrochloric Acid → HCID 15096839, compound

HRID 345604Notes

Reaction equation

HRID 345604 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:13][C@H:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][C@H:15]1[OH:27])=[O:12])(=O)C.[OH-].[Na+].Cl>>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:13][C@H:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][C@H:15]1[OH:27])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15097001HCID 15097001, compound

Product 1

HCID 15096839HCID 15096839, compoundYield 27%

Conditions

Temperature
60 °C

Procedure

A mixture of 5 parts of cis-2-[3-hydroxy-1-(phenylmethyl)-4-piperidinylaminocarbonyl]phenol acetate (ester) and 30 parts of sodium hydroxide solution 1N was stirred and heated for four hours at 60° C. The reaction mixture was cooled to room temperature and neutralized with a hydrochloric acid solution 1N. The product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated. The residue was purified by columnchromatography over silica gel using a mixture of trichloromethane and methanol (85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue solidified on triturating in 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.21 parts (27%) of cis-2-hydroxy-N-[3-hydroxy-1-(phenylmethyl)-4-piperidinyl]benzamide; mp. 127.1° C. (compound 235).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted with 1,1'-oxybisethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by columnchromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (85:15 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customon triturating in 2,2'-oxybispropane
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-365de9a5f8094ae1920a1f3821f1970d
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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