Hydrochloric Acid → HCID 18545677, compound

HRID 1267507Notes

Reaction equation

HRID 1267507 reaction equation
[CH2:1]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12](=[C:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=1)[CH2:13]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].Cl.CCOCC.Cl>CCOCC.CCO>[CH2:1]([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12](=[C:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=1)[CH2:13]2)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10953452Ether hydrochlorideHCID 69737456HCID 69737456, compound

Product 1

HCID 18545677HCID 18545677, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 22 g (0.048 mole) of ethyl 4-[(8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzoate, 86 mL of 3N NaOH and 200 mL of EtOH was refluxed for 1 h. After cooling the mixture was made acidic with conc. HCl. The solvent was decanted away from the gum which formed. The gum was titurated with Et2O and Et2O/HCl and was placed into a drying oven overnight at 45° C. to yield 19.2 g of 4-[(8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzoic acid; mp. 285-290° C. MS m/z (MH+) 425. 1H NMR δ 7.9 (d, 2H); 7.4-7.2 (ar, 12H); 3.7 (bs, 2H); 3.0 (bs, 4H); 2.8 (bd, 2H); 2.2 (t, 2H); 2.0 (m, 2H); 1.65 (m, 2H).

Workup

  1. temperaturewas refluxed for 1 h
  2. temperatureAfter cooling the mixture
  3. customThe solvent was decanted away from the gum which
  4. customformed

Sources & evidence

ORD record
ord-008de143938d4a8c927210bb11972287
Source dataset
uspto-grants-2003_04
Patent number
US06552036B2

Reaction notes

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