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Sodium Bicarbonate → Ahr 5333

HRID 1193687
Notes
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Reaction equation

HRID 1193687 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.[C:23]([C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][CH2:32][CH2:33]Cl)=[C:28]([O:37][CH3:38])[CH:27]=1)(=[O:25])[CH3:24].C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:33][CH2:32][CH2:31][O:30][C:29]3[CH:35]=[CH:36][C:26]([C:23](=[O:25])[CH3:24])=[CH:27][C:28]=3[O:37][CH3:38])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 173727Ahr 5333Yield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5.0 g (0.0165 mole) of α,α-bis(p-fluorophenyl)-4-piperidinemethanol, 4.0 g (0.0165 mole) of 3-(p-acetyl-o-methoxyphenoxy)propyl chloride and 1.4 g (0.0165 mole) of sodium bicarbonate in 60 ml of dimethylformamide was stirred and heated at 80° C. for two hours. The temperature was raised to 100° C. for one hour. After cooling, the reaction mixture was filtered and the dimethylformamide was removed at reduced pressure. The residual oil which crystallized on standing in ether was dissolved in benzene and placed on a Florisil® column. Using a gradient elution of acetone-benzene, 1.8 g (21.4%) of product was obtained from the column, m.p. 141.5°-143° C. (See Ex. 12, U.S. Pat. No. 3,956,296).

Workup

  1. temperatureThe temperature was raised to 100° C. for one hour
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe dimethylformamide was removed at reduced pressure
  5. customThe residual oil which crystallized
  6. dissolutionwas dissolved in benzene
  7. washa gradient elution of acetone-benzene

Sources & evidence

ORD record
ord-1b1cb94506a54477a446c4963513906a
Source dataset
uspto-grants-1989_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04810713

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes