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Sodium Hydroxide → HCID 12972366, compound

HRID 2297648
Notes
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Reaction equation

HRID 2297648 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OP(Cl)(OC2C=CC=CC=2)=O)C=CC=CC=1.Cl.Cl.[CH3:36][CH:37]1[CH:42]([NH2:43])[CH:41]2[CH2:44][CH2:45][N:38]1[CH2:39][CH2:40]2.[OH-].[Na+]>C1COCC1>[CH3:36][CH:37]1[CH:42]([NH:43][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)[CH:41]2[CH2:44][CH2:45][N:38]1[CH2:39][CH2:40]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 751824-Phenoxybenzoic acidHCID 75654Diphenyl chlorophosphateHCID 220470632-Methyl-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 12972366HCID 12972366, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

TEA (0.32 mL, 2.3 mmol, 1 eq) is added to a solution of 4-phenoxybenzoic acid (0.50 g, 2.3 mmol, 1 eq) in 15mL THF. Diphenylchlorophosphate (0.44 mL, 2.3 mmol, leq) is added and the mixture is stirred at room temperature. After 0.5 h, a suspension of 2-methylquinuclidin-3-amine dihydrochloride from Step N (0.49 g, 2.3 mmol, 1 eq) and TEA (1.30 mL, 9.2 mmol, 4 eq) in THF is added and the resulting mixture is stirred overnight at room temperature. 1N NaOH is added and the aqueous layer is extracted with CHCl3. The combined organic layers are dried over MgSO4, filtered and concentrated to provide 0.64 g (82%) of N-(2-methyl-1-azabicyclo[2.2.2]oct-3-yl)-4-phenoxybenzamide. MS (ESI) for C21H24N2O2 m/z 337.3 (M+H)+ . The fumaric acid salt of the product is made and crystallized from IPA to give the product as a white solid. Reverse phase HPLC (ZORBAX Eclipse XDB-C8, 4.6 mm×15cm, 75:5:20 H2O/CH3CN/IPA) reveals an 85:15 trans/cis mixture of isomers.

Workup

  1. additionis added
  2. stirringthe resulting mixture is stirred overnight at room temperature
  3. extractionthe aqueous layer is extracted with CHCl3
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-01056f9e3c72467ca4b408250c094c61
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06492386B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes