1-(4-BENZYLOXYPHENYL)-2-(4-HYDROXY-4-PHENYL-1-PIPERIDYL)PROPAN-1-ONE → HCID 15517720, compound

HRID 351992Notes

Reaction equation

HRID 351992 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:31])[CH:16]([N:18]2[CH2:23][CH2:22][C:21]([OH:30])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[CH3:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([O:40][C:41](=[O:57])[C@H:42]([C@@H:44]([C:46]([O:48][C:49](=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[OH:45])[OH:43])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CC(C)=O>[C:49]([O:48][C:46](=[O:47])[C@H:44]([C@@H:42]([C:41]([O:40][C:32](=[O:39])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:57])[OH:43])[OH:45])(=[O:56])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1.[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:31])[C@@H:16]([N:18]2[CH2:23][CH2:22][C:21]([OH:30])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[CH3:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 107405821-(4-BENZYLOXYPHENYL)-2-(4-HYDROXY-4-PHENYL-1-PIPERIDYL)PROPAN-1-ONEHCID 12858289HCID 12858289, compound

Product 1

HCID 15517720HCID 15517720, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
50 °C

Procedure

120 g (0.289 mol) racemic 1-(4-benzyloxy-phenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-1-propanone and 1360 ml acetone were charged to a 3 liter flask equipped with a mechanical stirrer, a thermometer and a reflux condenser. The resulting solution was warmed to 50° C., then 105 g (0.293 mol) di-O-benzoyl-D-tartaric acid was added followed by a 200 ml acetone rinse. The solution was stirred at 50° C. and a suspended solid formed after about 25 minutes. The suspension was stirred as an additional 5 hours at 50° C., and then the mixture was cooled to room temperature over 1 hour. The suspension was filtered and the solid cake was washed with 500 ml acetone. The solid was dried at about 45° C. under vacuum (10 mmHg) overnight, giving 191 g (86% yield) (2S)-1-(4-benzyloxy-phenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-1-propanone di-O-benzoyl-D-tartaric acid salt.

Workup

  1. customequipped with a mechanical stirrer
  2. washrinse
  3. customa suspended solid formed after about 25 minutes
  4. stirringThe suspension was stirred as an additional 5 hours at 50° C.
  5. temperaturethe mixture was cooled to room temperature over 1 hour
  6. filtrationThe suspension was filtered
  7. washthe solid cake was washed with 500 ml acetone
  8. customThe solid was dried at about 45° C. under vacuum (10 mmHg) overnight

Sources & evidence

ORD record
ord-eef9e126693a452da920611b332dbdb3
Source dataset
uspto-grants-2004_06
Patent number
US06743921B2

Reaction notes

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