Sodium Carbonate → HCID 20261613, compound

HRID 465018Notes

Reaction equation

HRID 465018 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=2)=[O:12])[CH2:4][CH2:3]1.[C:27](=[O:30])([O-:29])[O-].[Na+].[Na+].[C:33]1([CH:39](Br)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(C(C)=O)C(C)C>[C:20]([OH:22])(=[O:21])/[CH:19]=[CH:16]/[C:27]([OH:29])=[O:30].[C:33]1([CH:39]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[O:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([CH3:25])([CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:18]=3)=[O:12])[CH2:4][CH2:3]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 236603Bromodiphenylmethane2×HCID 20261592HCID 20261592, compound

Product 1

HCID 20261613HCID 20261613, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent3×

Procedure

To a mixture of ethyl 4-[4-(4-hydroxypiperid-1-yl)butyroyl]α,α-dimethylphenylacetate (18 g; 0.05 moles) and sodium carbonate (10.6 g; 0.1 mol) in methyl isobutyl ketone (100 ml), a solution of diphenylmethyl bromide (12 g; 0.05 moles) in methyl isobutyl ketone (50 ml) was slowly added and the resulting mixture boiled under reflux for 12 hours. Then another solution of diphenylmethyl bromide (6 g; 0.025 moles) in methyl isobutyl ketone (15 ml) was added and the mixture boiled under reflux again for 24 hours. The reaction mixture was cooled, washed with water, the solvent removed in vacuo and the residue treated with the stoichiometric amount of fumaric acid in ethanol. The obtained solid was recrystallized from methyl ethyl ketone and from ethanol to give ethyl 4-[4-(4-diphenylmethoxypiperid-1-yl)butyroyl]α,α-dimethylphenylacetate fumarate (5.6 g; yield 17.4%) which melts at 168°-170° C.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureunder reflux again for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. customthe solvent removed in vacuo
  6. additionthe residue treated with the stoichiometric amount of fumaric acid in ethanol
  7. customThe obtained solid was recrystallized from methyl ethyl ketone and from ethanol

Sources & evidence

ORD record
ord-52a95a1d3ab245fa82b3d43090bfe51f
Source dataset
uspto-grants-1985_10
Patent number
US04550116

Reaction notes

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