Benzoic Acid → HCID 89846704, compound

HRID 76384Notes

Reaction equation

HRID 76384 reaction equation
[OH:1][C:2]1([CH2:10][S:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[C:17]([OH:25])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[C:17]([OH:25])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH:1][C:2]1([CH2:10][S:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 86699444HCID 86699444, compound

Product 1

HCID 89846704HCID 89846704, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 3-hydroxy-3-[(1-ethoxyethyl)mercaptomethyl]quinuclidine (15.52 g, 63.3 mmol) was added toluene (75 mL). Benzoic acid (7.73 g, 63.3 mmol) was added in one portion. The reaction mixture was stirred for 18 hours and the white precipitate that formed was filtered and washed with toluene (3×30 mL) to give 3-hydroxy-3-[(1-ethoxyethyl)mercaptomethyl]quinuclidine benzoic acid salt (16.15 g, 44.0 mmol, 69%) as a white solid containing 10% toluene by weight.

Workup

  1. customthe white precipitate that formed
  2. filtrationwas filtered
  3. washwashed with toluene (3×30 mL)

Sources & evidence

ORD record
ord-82594633e38941098103fa9be45bdb65
Source dataset
uspto-grants-2014_09
Patent number
US08835638B2

Reaction notes

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